Not a day goes by since I wrote that post (I have the tracking stats to prove it) that at least a few people don’t find my article via a Google search, which means people have been frustrated with this issue and have been looking for solutions for a very long time. Some have even reached out to me to thank me for reassuring them they aren’t crazy.

Imagine how my ears pricked up, then, when rumors started floating around this year that Apple was poised to retire iTunes in the next major version of macOS? While many were frightened Apple was taking away their precious music player of choice, I was elated at the chance of a brand new app which would presumably not elicit this same bug. After all, the rumor originally figured the new Music app would be ported over from its iOS counterpart on the iPad. And the iPad version doesn’t have this bug.

But then Apple announced Music for macOS (which will ship this fall with the Catalina update), and it quickly became apparent that rather than a complete rewrite, the app would simply be iTunes with a new name and a lot of its more bloated features removed.

Happy as I am to see the bloat removed, and as much as I believe strongly that you should not throw away perfectly functioning code for no good reason, the code in iTunes was far from perfectly functioning.

So, the big question: Would this bug still be present in Music, despite all the work Apple had put into rebranding and reworking it?

Luckily, I don’t have to wait until September to find out. I’m an Apple developer, after all, so I get early access to the beta versions of this software.

So I installed Catalina’s beta onto my Mac, fired up Music, turned on the iCloud Music Library feature, and…

Well, at first, the duplicates appeared again. I was despondent. I could not believe Apple didn’t bother addressing this issue after at least one-and-a-half years. (In all likelihood, the bug has been around quite a bit longer than that.)

But then, a few moments later, something wonderful happened. All the duplicate tracks disappeared in an instant. It was if Music caught itself making the same old mistake, and then corrected itself.

As of this writing, the duplicate tracks are still gone. iCloud Music Library is functioning on my Mac as intended. And any new tracks I download are being synced perfectly between my iPhone and Mac.

Fingers crossed that all is well, and we will finally be able to call this bug defeated.

I say will be, of course, because Catalina is not shipping yet. Those of you who are not developers will have to wait to get this fix. And there’s always the chance that the bug will return before shipping. But I highly doubt it. I think there are going to be a lot of happy Music users come fall.

Fall is here, and that means it’s time for yet another chapter in Joe’s Adventures of Getting His iTunes Music Collection onto His New iPhone.

Don’t worry: This one has a mostly happy ending.

Long-time readers will recall past issues with getting my music situation settled on the iPhone every year. Here’s the short version:

• I want ALL my music on my phone, downloaded, and ready to play. I am away from internet connectivity often enough (on the subway, on airplanes, and so on) that having local music at the ready is essential. I do not like choosing the music I might want to listen to two days before I go on a trip. Call me crazy, but I expect my music experience in 2018 to be as good as what I had with my iPod back in 2002.
• I have tons of music in my iTunes library. Hundreds of gigabytes worth. Tens of thousands of songs.
• Much of the music in my library is from iTunes. Much of it is not. I’ve ripped old CDs, downloaded tracks from indie bands, bought tracks from other online services, etc.
• A good number of my tracks are not available on iTunes. Either they never made it there, or they have since been taken down. Most of these tracks are obscure stuff from unsigned bands or alternative releases that are only available in physical form, etc.
• In a new twist for this year, I’m now an Apple Music subscriber. I use the service mainly for discovery, and so I can ask HomePod to play things for me very easily. But I still want to keep my precious collection of owned music safe and secure, in case I ever stop being an Apple Music subscriber.

If any of the above sounds familiar, congrats. You are as odd as I am when it comes to music. I get that most people don’t care about locally stored songs, and they listen to the same five tracks over and over again for several months at a time. Congratulations to them. Apple has you well covered. For the rest of us, getting our peculiar musical needs met takes a bit more effort.

This year, because I’ve added Apple Music into the mix, and along with it iCloud Music Library, I had to change up my methodology a bit.

I won’t go into why here, but you can read all about why I use iCloud Music Library on my phone and iPad, but not my Mac. Unsurprisingly, that bug has still not been addressed.^[1]

So here’s what I did. I’m happy to report this worked out very well.

Step One - Get a new phone, but leave music alone

I tend to order my new iPhone for pickup at the retail store. I like to get up in the morning early, head down to the Upper West Side, pick up my phone, and get home by 9am or so.^[2]

When I got my new phone this year, I restored over the wire from a backup I made on iTunes that morning. This is preferable to an iCloud backup in a few fundamental ways. First, it’s encrypted, which means all my passwords to my apps come along for the ride. I don’t have to spend the majority of my day launching apps and logging back in. I may have to reauthorize FaceID a few times, but overall it’s far smoother. Second, it’s much faster than an iCloud backup.

iCloud backup is great for daily backups and emergencies. For a new phone, I highly recommend running an iTunes wired backup of your old phone just before purchasing.

Once my backup was restored, I waited for my apps to download, then went about my day. I made no attempt to get music onto my phone, unless it was to download an album or two to listen to while working. The real process was going to have to wait until bedtime.

Step Two - Get any music that was inadvertently downloaded off the phone

Just before bed that first night with my new phone, I went into Settings > Music > Downloaded Music and erased any songs I had downloaded throughout the day. This is to prevent accidental duplicates. Then I went to Settings > Music and turned off iCloud Music Library. This is necessary for allowing my Mac to transfer files to my phone manually. (Remember, I keep iCloud Music Library off for my Macs, for reasons stated here.) I also double checked to be sure Optimize Storage is turned off.^[3]

Step Three - Plug into iTunes and get ready to drag some music

Next, I plugged my new phone into my MacBook Pro and fired up iTunes. I made sure I had music selected from the category selector. Once the phone was recognized, I could see it in my Devices list on the left. I selected artists from the Library list (you could just as easily select songs if you like), selected ALL of the tracks by first selecting a track, then typing Command + A to Select All, then dragged all of those files over to On My Phone.^[4]

After a few seconds of waiting, the head’s up display on iTunes confirmed that the files were indeed beginning to copy.

Step Four - Go to bed

Seriously. In the case of my library, this was going to take a few hours. There’s a reason I do this at the end of the day.

Step Five - Confirm everything has copied

The next morning, I awoke to find that all of my files had copied over just fine. No error messages on my Mac, and a quick trip to the Music app on my phone showed tons of tracks in the Downloaded Music list. Long-time readers will understand why this made me so happy. If you’ve been dragging and dropping from iTunes to phones over the years, you’ll know that this hasn’t always been a guaranteed outcome. I am glad to see that this is still working perfectly in the latest iTunes and iOS versions.^[5]

Step Six - Re-enable iCloud Music Library and do some downloading

Now that my entire library from my Mac was on my phone, I wanted to get iCloud Music library up and running again. That’s as easy as going back to Settings > Music and flipping that switch back on. The phone will ask you if you want to keep the music you’ve already got on your phone. Make sure you do that, or else you’ll end up with no locally downloaded music again. I worried for a moment that I may end up with duplicates in my iCloud Music Library as a result of this, but so far that does not seem to have happened.

Finally, I went to the Music app on my phone, scrolled through the recently added section, and downloaded those few albums I had downloaded recently on my old phone for discovery. Those tracks aren’t on my Mac (thanks to the fact that I can’t run iCloud Music Library on my Mac), so I needed to bring them back down onto the phone manually. Not a huge deal, compared to downloading everything that is on my Mac manually.

Conclusion

Compared to previous years, where I’ve spent several days or even weeks trying to get my entire library to my phone, this worked out great in one night. It would be a bit easier, of course, if Apple fixed the iCloud Music Library duplicate issue on the Mac. But for now I’ll take it.

I’m sure I’ll discover an album or two I had downloaded to my old phone that I’ve forgotten to re-download on the new phone. I figure that will be a minor annoyance compared to years past.

Hopefully, if you’ve got a bug up your ass about music like I do, this method will help save you some agony.

Update: It looks like Apple may finally have fixed this bug in the next version of macOS, called Catalina. Read more details in my new post here.

Over the years, the majority of my complaints about Apple have centered around music. That’s because I love music, and Apple clearly doesn’t always think enough about people outside of its contrived all-in-on-Apple-Music listener when it comes to the iTunes experience.

Today’s complaint actually begins with a recent positive discovery. I finally gave in to the temptation and signed up for a free trial of Apple Music, and it’s really great. The recommendations it makes are often good, or at least not terrible, and I love being able to try out lots of artists that I otherwise would probably not have discovered. I love downloading tracks on my phone as I discover them, and I like listening to them even when I’m offline. So far, so good. I definitely plan to remain a subscriber.

But then I ran into a bit of a snag when it came to the iCloud Music Library. This is the feature that syncs whatever you put on one device with all your iPhones, iPads, Macs, etc. In theory, it’s a great idea. If I discover a track on my iPhone and download it, it’ll be sitting on my Mac next time I might want to listen. And vice versa. On my iPad, I don’t auto-download these tracks, but they show up in my library for streaming if I want them. Perfect.^[1]

But after a couple of days of enjoying this new iCloud Library experience, I noticed a problem on my Mac. In iTunes, every track that is available on Apple Music but that I had acquired elsewhere (CD Rip, purchased from another store, etc) was doubled in my iTunes library. Each song would be listed twice, in other words.

In some cases, one version would have a little cloud icon with the down arrow, indicating that it can be downloaded from iTunes, and the other would have a cloud and an X, indicating a track that is from my library, already downloaded, but not from iTunes. On my phone and iPad, these tracks only show up once. But on the Mac, there were two. Right after one another.

In other cases, it would actually download the second copy, so I’d get one track with no icon (downloaded from iTunes) and the other with the X (my original file). All of these files were taking up twice as much space on my hard drive.^[2]

File size issues aside, you can see how this would be a problem for someone like me who likes listening to albums. Unless I want to hear each song twice in a row before advancing to the next one, I have to remove all the duplicate tracks from Up Next every time I click on an album. (Even the ones that aren’t yet downloaded just stream when I play the album.)

Well, that’s a strange bug, I thought. Maybe I should throw away the extra downloaded ones and just leave my original tracks. We’re talking about thousands of tracks, so that would be a lot of work. But if it’s just a one-time glitch, so be it.

When I attempted to remove a cloud track however, I got a warning that it would remove the track on my phone as well. That’s not good. I want the track to stay on my iPhone. I just don’t want two copies on my Mac.

The other option, of course, was to erase my copies of the tracks and just leave the cloud versions. Which means if I ever cancel Apple Music, those tracks will likely be gone forever, since I didn’t buy them on iTunes. They would not be part of my purchase history, so they would disappear, along with everything else I try in Apple Music.

This is not an option.

So I found a third alternative: I just turned off iCloud Music Library on my Mac. The duplicates immediately went away, and I was left with my old library intact. I miss out on syncing new tracks that I find on my phone, but those can be found and streamed on my Mac from the recents section of For You. Terrible user experience, but at least there’s a workaround.

Believe it or not, I wasn’t driven to write a long tirade yet. I tweeted something snarky, but then I let it go. Lots of others informed me this has been a known issue for quite a while. Yikes.

And then something happened this week, when one of my favorite bands, Big Big Train, released a pair of new Christmas songs. Only one is available on iTunes, while the other is a special b-side you can only get from their web store. A portion of the proceeds from those songs also gets donated to charity when you buy on their store. So I bought both tracks on their store, of course.

I often buy tracks from indie artists on their own sites, anyway. As an extra sign of support. This is not weird or extremely unusual behavior. It’s pretty common for music fans.

It’s when I tried to listen to these tracks that I found my inspiration for this rant. I could add these two new tracks to my Mac, no problem. But because I didn’t have iCloud Music Library turned on, those tracks were not synced up with my phone. Okay. I can just plug my iPhone into the Mac with a USB cable and drag the new tracks over to my phone, right?

Nope.

Because iCloud Music Library was turned on for the iPhone, I was now no longer able to simply drag and drop files between the Mac and iPhone. iCloud Music Library is an all-or-nothing proposition. The only way to get these two tracks onto my phone would be to either turn off iCloud Music Library on the phone (and thus lose all the Apple Music tracks I’ve downloaded) or turn iCloud Music Library back on for my Mac, and let the tracks sync.

I chose the latter, which, of course, brought back all the duplicate tracks on my Mac as well. So then I had to turn off iCloud Music Library on my Mac after the upload of my new songs made it to my other devices. Fortunately, the two new tracks remained on my phone.

You read that right. Moving forward, whenever I get a new audio track that isn’t from Apple Music, I’ll have to add the track to iTunes, turn on iCloud Music Library on the Mac, let it upload that new track to the cloud and download all these thousands of duplicates, then turn off iCloud Music Library on the Mac to remove all the duplicates.

Lovely.

I purchase the vast majority of my music from the iTunes Music Store. I shouldn’t be punished for occasionally getting tracks from other sources. Especially when those tracks aren’t even available on iTunes.

All of this suggested to me that perhaps no one at Apple has any music that wasn’t downloaded from iTunes? Although that can’t be true. You’d think someone in charge of music over at Apple had listened to music prior to the iTunes Store’s existence, which means they at least have some tracks that were ripped from CDs in the early 2000s. Given this issue is so thoroughly annoying, I would think it would have gotten fixed somewhere in the last year or two once someone noticed, right? It’s simply not possible that no one over there has noticed this problem.

The only other two conclusions I can make is that no one at Apple cares (not likely) or that this duplication of tracks is somehow intended. Which brings me to my favorite question: Why? Why would anyone want to search through their entire library and delete all these duplicate tracks? Or erase their entire music library before signing up for Apple Music, so their library would be fresh and only sourced from Apple?

If the Mac can detect that I have a track in my library that’s from another source but also available on iTunes, why can’t it just mark that track as already downloaded, and then just download a copy to my other devices? Like I said, this works just fine on my iOS devices.^[3]

Despite my frequent complaining, iTunes has improved over the years. So many things that used to drive me nuts are better at this point. I’m back to using the built-in iOS Music app again. I recently wrote about drag and drop from iTunes to your iOS devices finally working reliably. I can finally sort albums on my phone by date instead of title. I signed up for Apple Music and I actually like it. Apple is working on making these experiences better. Maybe this duplicates issue is just another item on a long list of things to be fixed, and we’ll eventually see it go away. I have to hope so. It’s one of the few remaining big ticket items that leaves me scratching my head at an otherwise decent music experience.

Progress has been very slow going, though. I’ve already volunteered, if Apple ever wants to take me up on it, to help them find any remaining issues by examining my music library. If they want to find music-lover use cases they probably haven’t considered, my hard drive is full of them. Heck, I’m usually in the Bay Area at least twice a year, anyway. I’d be happy to stop by whenever they want to talk.

While everyone else in the community is still losing its mind over the battery bump, I thought I’d offer a change of pace and criticize something a little more concerning about Apple’s recent endeavors. It didn’t take much effort to find something less controversial, at least.

Let’s take, for instance, the experience of watching iTunes Extras material on an iPad.

iTunes Extras are like DVD bonus features for the movies you buy on iTunes. Some movies only offer an alternate commentary track. Others get quite elaborate, with tons of deleted scenes, interviews, mini-features, the whole nine yards. I’m a big fan of the concept. I am a huge nerd, after all.

A few years ago, you could only watch this bonus stuff on your Mac, which was stupid. Then in 2014 Apple gave iOS the ability to view them again, which was welcome news indeed. Why would I want to watch several hours of video content on my Mac instead of my TV or iPad? Seemed like a no brainer, so I was glad Apple was going to correct this silly omission.

So what’s the problem, Joe? Apple gave you what you wanted, right?

I’ll just make a bulleted list, to keep it simple:

• iTunes Extras are streaming only. Can’t download them to the iPad. So, no broadband Internet connection at the time you want to watch, no Extras. You can forget about queuing those 90 hours of Hobbit Appendices for your flight to New Zealand, even though you ponied up the extra cash for a 128GB iPad.[1]
• Where do I find the Extras? There’s no Extras button on the main movie launch screen. First hit play on the movie, then, if you happen to have an Internet connection, and you happen to notice before the controls fade away, there will be a button for Bonus Features on the bottom of the screen below the playback controls. It’s as if Apple is afraid you might actually want to watch this stuff.
• Enter the Extras, use the menu system, hit play on one of videos. About two minutes in, it’ll pause, as the connection struggles to keep up. This will happen several times while you’re watching no matter how good your broadband is. All part of the experience.
• Pause the Extra, put the iPad to sleep. You’ve now lost your place. You’ll have to start the entire process over and guess where you were in the video you were watching, if you can remember which one you were watching, that is.
• Tap on a notification to jump to another app really quickly. You’ve now lost your place. See above.
• This one is my favorite: Rotate the iPad so that you change orientation.[2] You guessed it, you’ve now lost your place. The video will switch over to the main feature movie and play that. Because that makes perfect sense.
• Pause the Extra and hit the home button. It’s okay. You can say it. You’ve lost your place yet again. Only it gets even more interesting. Now, the audio of the main movie feature will begin to play, in the background. Ironically it’ll start where you left off the last time you watched the actual movie, just as an extra kick in the nuts. Open up the video app, and sure enough, the main feature movie is now playing. Hit pause, go do whatever you wanted to do, then come back and start all over again.
• Try scrubbing through the Extra you were watching, and the experience makes the old AppleTV scrubbing seem fluid by comparison. Slide to 8:42, the playhead will jump to 6:23 for no reason. Try to push it back to 8:42, it’ll jump to 11:47. Push it back again, let it jump to 5:50. At this point you’ll just watch it again from the beginning until you get back to where you left off.

I suppose all of this is better than having no ability to watch the Extras at all on mobile, but not by much. After all, if you have a perfect Internet connection, and you want to watch the Extras all in one shot without pausing or getting interrupted for any reason, then it’s just peachy, as long as you don’t mind the occasional pause for the connection to catch up. I’m sure this is how it was tested before being approved for release.

These are not hard bugs to find. They have been present for a while. Either no one is watching iTunes Extras content on their iPads except me, or Apple considers it a super low priority. Which is fine. But it is an embarrassment. Much more so than an ugly iPhone case, at any rate.

1. I went back to 64GB on my iPad Air 2 for this reason alone. Unfortunately, with the Pro, the only option, if you want the broadband necessary to watch iTunes Extras, is to also get 128GB of storage that you won’t be able to use to store those Extras.  ↩
2. This is something that happens unintentionally sometimes, like, you know, if you happen to be watching in bed and forgot to lock orientation as you change positions. That’s only happened to me about six thousand times so far, so it’s no big deal.  ↩

Ping: What went wrong | Macworld: “And therein lies Ping’s primary defect. Though dressed in social garb, at its heart, it’s a crude advertising vehicle. And one—undoubtedly to the great disappointment of some at Apple—that too many people saw through.”

(Via Macworld.)

Another great article from Christopher Breen. I’d add that another of Ping’s shortcomings is that you can’t simply post links to interesting articles, stories, pictures, etc. Artists could post whatever they wanted, but regular users like you and me had to start every conversation with a link to a song in iTunes. Talk about “marketing smell.” That limitation was just plain stupid.

Part of me thinks that any social network that tries to limit people to just talking about music is doomed to fail, anyway. I mean, I love music more than the average person, but I don’t always want to share only music. Sometimes, I want to share stories about music, apps that help you make music, books on the subject of music, pictures of my favorite bands, etc. The reason Facebook works so well is that you can literally share anything about anything. Sure, this leads to a lot more noise than signal, but it also encourages participation. I have a hard enough time finding things that I find post-worthy on a social network without the network itself telling me what I can and can’t post.

I know the current trend is towards more targeted social networks, but that’s simply a reaction to Facebook’s monopoly. I have to think that most of those mini networks will either be acquired by Facebook or die from lack of participation eventually. A small, targeted audience can’t live on advertising as easily as Facebook. You’ll never have a big enough audience to pay the bills.

iTunes: Time to right the syncing ship | Macworld:

The iTunes we’ve all come to know has had a good run, but it’s reached the point where it is a crazy agglomeration of features and functionality. If someone were to design it today, it wouldn’t remotely resemble its current state. And as a portal to iOS devices and the iTunes Store, iTunes is too crucial to Apple’s business to ignore or run on auto-pilot.

(Via www.macworld.com)

I think just about everyone who uses iTunes, which is everyone, agrees with the sentiment here. iTunes is definitely over bloated, and it’s trying to do way too many things at once.

But I think it was John Gruber who pointed out a while ago that iTunes is one of very few cross-platorm apps for Apple. The reason they packed so much into that one app is that they don’t want to be in the business of building and maintaining several Windows apps. Sooner or later, something is going to have to give, but that’s how we got here, anyway.

What I do is limit my need for iTunes as much as possible. Podcasts? I use Downcast for that. Movies and TV Shows? All done with iCloud on my Apple TV and iPad at this point. Photostream and Dropbox takes care of most of my photo needs.

So the only thing I really sync with iTunes anymore is music. I could use iTunes Match for that, of course, but that’s still so buggy I can’t rely on it. I expect that will get better over time.

I think Apple’s strategy isn’t to break up iTunes into several new apps, but rather to eliminate the need for iTunes almost entirely. Turn it back into a simple music store/music player for the Mac, and replace everything else with iCloud.

We’re just not quite there yet.

Here are some of the most common queries, concerns, and misconceptions about Apple’s music service, laid out for your reading pleasure.

via iTunes Match: What you need to know | Macworld.

Macworld wrote a nice article here clearing up a lot of the misconceptions surrounding iTunes Match. I think this is a classic case of people hearing what they wanted to hear back when Apple announced this service. Many had it in their heads that it was some grand Cloud strategy that would allow them to no longer store any of their music on their devices, and just stream it all at will from anywhere. And that’s not really what iTunes Match is.

Which is why I questioned the value of iTunes Match when it was announced, and everyone else seemed to think I was crazy.

The way I see it, there are only two reasons to become an iTunes Match member, and only one to become a long-term subscriber.

1. You have a lot of songs in your iTunes library that are lower quality than 256 AAC, and you want a quick and cheap way to upgrade all those tracks to better-quality versions.

2. You have a lot of obscure music that isn’t available on iTunes, and you’re too lazy to set up music synching with your computer and let it sync once.

The first reason turned out, to my surprise, to be enough for me to sign up, at least for one year. I don’t plan on re-subscribing next year, as reason 2 doesn’t apply to me. But I found that I did indeed have a lot of tracks (over 7,000) that were either ripped from my CDs prior to the iTunes Store era, in which case they were mostly MP3s, or, and this was the kicker, bought prior to Apple’s switch over to iTunes Plus, in which case they were still encumbered with DRM and only encoded at 128k. Apple has long had a service whereby you could pay 30 cents a track to upgrade your old purchased tracks to 256, non-DRM versions, but with the size of my purchased library, I was looking at over $350 to upgrade all my older tunes to iTunes Plus. So I never did. And that would leave my old CD rips out, as well. Being able to upgrade all those tunes alone made the $24.99 for one year of iTunes Match a no-brainer for me.

For those of you who never paid for your music back in the Napster era, think of iTunes Match as a one-time $25 fee to make as much as 25,000 songs of that music legit, no questions asked. My guess is that if you didn’t value the music enough to pay for it back then, you won’t now, even at that bargain price.

Beyond upgrading old purchased and CD tracks to 256k, though, I don’t really see the point of iTunes Match in the long run. Because, and here’s where the confusion comes in for a lot of people, it’s not a streaming service. There’s a streaming component, but it’s not the primary focus.

Sure, you can technically stream songs in iTunes that aren’t on your computer. And your AppleTV, which doesn’t have a hard drive, will stream your music as well. But that doesn’t make iTunes Match a streaming service. Rather, it’s a service that happens to stream sometimes.

iTunes Match is essentially iCloud for your music. Like iCloud, there is a copy out there in the Cloud for you to grab and pull down to any one of your devices. But the focus is still on the local copy of the file. On iOS devices, if you listen to any iTunes Match track that isn’t currently on the device, it doesn’t stream; it DOWNLOADS the track and leaves it on the device after you’ve listened. It plays the local copy, not the Cloud copy, in other words.

And, to be honest, that’s the way I want it. I don’t live in this fantasy world where I’m connected to solid, uninterrupted 3G or Wifi 24-hours a day. In fact, where I listen to music the most (on the subway, walking around downtown San Francisco, and in many cafés) I’m connected to neither 3G nor WiFi quite often. So a Cloud-only music service would be fairly useless to me. I’d be without music a majority of the time.

Downloading the occasional random track that I didn’t think I’d want while I was around my computer last is a nice bonus, sure. But the chances that I’ll want to do that often enough to justify $25 a year are slim.

I’m perfectly content with going to iTunes on my computer and telling it to sync my music over WiFi once. After that, everything I buy new on the iTunes Store gets downloaded automatically to all my iOS devices, anyway. And all my past iTunes purchases can be downloaded with a tap, no iTunes Match needed. It’s only my old CD rips that won’t be available in the cloud after my first year is up. No big deal to me.

If the majority of your music isn’t from iTunes, AND it’s obscure enough that iTunes Match won’t even recognize it, AND you still want to be able to download it at will, then sure it makes sense to keep subscribing year after year to iTunes Match. Otherwise, sign up for the first year, get your lower-quality tunes matched up, and then you’re good to go.

If you’re really looking to store no music on any devices, and you just want to stream everywhere all the time, then Apple isn’t where you want to get your music. Spotify, Rdio, Pandora, etc. are the way to go for you.

If you’re a quality nut, and you only want songs ripped in pristine AIFF or Apple Lossless, no Cloud service is ever  going to be for you. You’ll be manually syncing forever.

If you have more than 25,000 tracks, you should seek professional help. You’re a collector, not a listener. No one who owns that much music has listened to it all once, let alone enough to appreciate it.

Why so many people seemed to think that iTunes Match was going to be everything for everyone is a mystery to me. As I said before, I think a lot of people heard what they wanted to hear, rather than what was actually being announced.