As you know if you’ve read much of my writing, I’ve become a huge Apple convert. In general, the ease of use that Apple has brought to the consumer, the jaw-dropping delight of their product design, and the completeness of support for the developer have impressed me to no end. However, as a long time seeker of the ultimate “my music everywhere, anytime” solution, I am just plain pissed-off at the fail that is iTunes + iCloud + iTunes Match. Finally, with the introduction of iTunes Match, I thought this is it. Everything in the cloud, streamed on demand. No need to ever be missing music anywhere. This also allowed me to have all of my music in the car. Great, so we went through the laborious process of syncing up all of our itunes clients to ITunes Match. All is well. But there are some huge misses that make this not work. First, the relationship between itunes accounts and itunes libraries breaks with iTunes Match. Clearly my entire family, and all of their devices, should have access to all of our music. Apple’s current model is that iTunes Match is a one account solution. This means that I can’t use itunes accounts for tracking kids gift cards and monitoring spending, without having to download, copy and re-match the media my kids purchase. Second, Apple assumes that I’ll use the same account for music, apps, movies, cloud backup, calendars and email. Its possible to fudge this so that you get the right outcome (sync with my account for contacts, backup and calendars, and sync with a different account for shared media), but it isn’t the right model. Doesn’t anyone working on itunes have a family? This all worked fine with shared libraries, but we lost a level of containment with iTunes Match. I understand that Apple has to get around DRM requirements from the publishers, but frankly, I don’t care. Third, USB connections to the phone or iPad are built into all new cars these days, and they are wonderful - at browsing the music that IS ALREADY DOWNLOADED ON YOUR PHONE. Itunes Match simply doesn’t work at all when connected, and you can no longer control from the phone. Fourth, maybe #3 would be ok, except that there isn’t any great way of seeing what is on your phone and what needs to be downloaded. The only way to do this is to change your Music settings to turn off “show all music” and then going back into the music app. Why don’t I have the download status of albums and individual tracks available by default? Yecch. Fifth, let’s say I’m willing to get around the USB limitations by using bluetooth, well, that does allow me to choose any audio from my phone (now looking at the phone while driving - Danger Will Robinson), but it does not allow me to browse using the touchscreen built into the car. To be fair this may be a Toyota issue, though I’ve had it in every car I’ve rented as well. Sixth, the cloud isn’t available in many places, and iTunes Match pretty much needs LTE to not cut out. The music app is clearly not designed to gracefully degrade when losing connection. It just sits there like an idiot, occasionally blurting a second or two of music. Seventh, on the desktop I can get live streaming radio through itunes. Why can’t I get this on the phone? I hate the static of fm, and I hate having to switch interfaces. Finally, the most natural, easy, wonderful feature of Siri is to be able to tell her what song, artist, or album to play while I am driving. But, Siri is just as dumb as the USB and bluetooth interfaces. Clearly she’s actually searching the contents of the filesystem, rather than the itunes match directory - WHICH MY PHONE ALSO CONTAINS. Yikes. So my prescription for Apple is simple: 1. Allow multiple accounts to access the same itunes match collection. Work it out with the publishers, or we will all leave to a vendor that lets us access all of our music. 2. Fix the broken directory issues that plague siri, bluetooth, and usb connections. 3. Add icons to the music app that mirror the cloud status info you have on the desktop. 4. Give me a quick switch inside the music app that filters by cloud status. 5. Degrade gracefully when losing connection for more than a few seconds. Allow lookahead caching so that you store up tracks on my current playlist or album, and let me know when the cloud isn’t available. You could even offer me something that is resident from my genius match. 6. Add radio and podcasts to the mobile app. THE LONG QUEST FOR ALL THE MUSIC EVERYWHERE, ANYTIME For those who are interested, here’s the brief version of my historical efforts to have all my music with me all the time. For the longest time, I’ve been trying to get a solution where I can play music anywhere in my house, and control it from anywhere in my house, office, or car. Initially, I did this with an Escient device controlling two Sony 300CD carousels, and IR repeaters for my remote controls. Car access still relied on bulky folders of CDs. Later, I replaced the Escient with a WinAmp database and apps running on old laptops stationed around the house, and even an app on my HP Portable PC phone (remember those?). I bought a Jukebox hard drive which could store 5G of music, but never ended up using it much as it was bulky and incredibly error prone. When I moved everything to itunes, I initially used the same old windows laptops as the control interface. Once Apple added library sharing, I bought a few Roku units to interface to the stereos. It all worked, but intermittently. I adopted the AppleTV 1.0 mainly as a nice itunes client for my entertainment center, got a couple of Airport Expresses, and ditched all the windows computers. Much better, but still intermittent issues with wifi bandwidth. With home sharing, and the remote app on ipad and phones, I finally got the controllability that I wanted, but speed and bandwidth issues meant that playing music in my media center downstairs didn’t work as well when streaming from an external hard drive upstairs. With iTunes Match, I finally have controllability, portability, and completeness. And I have no need to pay a premium for devices with extra storage.