iTunes Match, Spotify, Rdio, and the search for a life in the cloud

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I've recently had to face the facts. My system for consuming music, a favorite pasttime of mine, is a complete and utter mess. It's broken, and I don't see an easy solution to fixing it.

Some background — I've been using iTunes to manage my music for nearly a decade, happily syncing away over a cord to my iPod (then iPhone) until the last two years or so. Lots of people have problems with iTunes, many of them with good reason, but for the most part it works for me. I grew up BUYING MUSIC — I had a pretty large CD collection when I was younger, and shifting that collecting mindset over to digital files just made sense and worked for me for a number of years.

However, this world of clouds and streaming and Rdio and Spotify and iTunes Match and Amazon Cloud Player have made things more complicated. I could just keep buying (or otherwise acquiring) digital albums and manually sync that content from iTunes to my iPhone, but I don't want to! I want the promise of the cloud, of all my music at my fingertips, just a stream away. Unfortunately, the reality is a way's away from the promise — maybe I'm too picky, but I keep finding fatal flaws in every attempt I make to move to the cloud.

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My first serious foray into cloud music was with iTunes Match. As someone well-entrenched in Apple's ecosystem, it made a lot of sense to give it a try; while there's some things about it I enjoy, ultimately it's an exercise in frustration. One thing that does work great is being able to get my entire library on multiple computers — my iMac houses my entire library, and I can access all of it easily on my laptop, even though most of it hasn't actually been downloaded to the computer. While my 120GB music library isn't huge, it's big enough that I like not having to replicate it across machines if I want to access it.

The problem starts when moving over to iOS; it's a two-fold issue split between Apple's implementation and Verizon's dog-slow 3G network. For one reason or another, downloading music to my iPhone over iTunes Match has always been a buggy, difficult experience. This morning I decided to try and make a move towards using iTunes Match full-time rather than syncing from my computer — but I keep getting met with "this song is not available for download" errors. It doesn't happen that frequently, but if I can't download what I want when I want to, the service is useless. Furthermore, navigating through the music app when iTunes Match is activated feels like scrolling through molasses. It isn't fluid or well-tuned, unlike most other pieces of iOS — and I'm using Apple's flagship mobile hardware. Something about this doesn't add up to me.

Verizon's 3G service in Boston brings me back to the days of using EDGE on my 2007 iPhone

Plus, the download speeds I get on Verizon's 3G network near Boston are positively wretched most of the time (seriously, it's almost as bad as EDGE was back on my 2007 iPhone). Trying to access anything in iTunes Match when out and about is a complete exercise in frustration. I might as well not even have a connection — it's Wi-Fi or bust.

My next instinct is to forget about iTunes Match and go all-in with one of the big streaming services. Most people I know use either Spotify or Rdio, and I've used both extensively, but unfortunately can't settle on either one as a full-time solution - partially because I'll always have music that isn't on one of those services (which means I'll still be using iTunes and Apple's default music app to some extent), and partially because each service has some annoying omissions that makes it near impossible for me to commit to one or the other.

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On the surface, Spotify seems like an obvious solution — it has a huge catalog and a robust user base to match. Plenty of my friends use it, so I won't be hurting for social interaction when using it. There's the potential for interesting extensions on the platform thanks to its push into apps. Most importantly, the music quality (both streaming and when synced) is damn good.

However, as mentioned earlier, I'm a collector. I believe in the album, and when I find an album I like, I want to be able to access it again easily. Sadly, Spotify has no concept of the album — the entire interface is built around playlists. For some months, I used Spotify, and just made a playlist for every single album that I discovered and might want to sync to my phone (or easily access when at my computer). Eventually, this just drove me mad — it's just ridiculous that there's no way to build up a music collection without adding everything to a playlist.

There's a few other downsides to Spotify, as well — the artist / song / genre radio stations are just not that great, the mobile apps are just not great, and you can't access anything through the web browser. That said, I'd live with all of these issues if Spotify would just fix the damn collection issue.

Which brings me to Rdio. All in all, this is the closest solution I can find. A lot of my cohorts use it, the desktop and moblie apps are quite a bit better than those by Spotify, and you can easily save an album to your "collection" and access it again without having to search or make a ridiculous number of playlists. It even scans your library and imports your iTunes music into your collection — and while it's a bit of a buggy procedure, it does give you a nice base of music to work with. Syncing to mobile is an absolute snap, and it downloads over Wi-Fi and 3G much, much faster than iTunes Match.

Listening without gapless playback is like stubbing your toe at the beginning of every song

My latest plan was to just move everything into Rdio — use the service exclusively, except for music that isn't available. I'd still be fragmented between two platforms, but I could probably live in Rdio 75 percent of the time, or maybe more. Most of the stuff I have in iTunes that isn't on Rdio is fairly obscure, random stuff — a live album here, a weird mix compilation there — so it won't mean I'm constantly flipping back and forth between apps.

Of course, there's a flaw. Rdio has no gapless playback! Not on the desktop, not on mobile, even with synced music (a problem that also plagues Amazon's recently-released Cloud Player for iOS). Listening to any album with songs that flow right into the next is now like stubbing your pinky toe at the beginning of each track. It certainly isn't crippling pain, and you forget about it quickly — but damn does it hurt at the time.

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After writing this all down, I have half a mind to just cancel Rdio, plug my iPhone into my computer, sync some playlists, and call it a day. Free Rdio and Spotify services can help me try new albums and recommendations from friends before making a financial commitment, and buying stuff I actually like on iTunes means it'll automatically show up my computers and iPhone without any trouble. Of course, I'll be spending a lot more money on albums than if I just ate at the monthly buffet of the streaming services, but a little sanity might be worth that cost.

Sound off below — what's your digital music strategy? Do you juggle multiple services, or have you managed to find one to go steady with?