Not quite sure what you mean. Match makes ALL of your music, playlists, metadata, etc exactly the same no matter what device you access it from. What are you trying to keep track of?
What music is available when I'm offline.
The music that you've chosen to download to the device. While online, you can turn off displaying music that isn't on the device so there's no confusion.
Right, but I have playlists setup like "Recently Added" so that songs I add are automatically put on my iPhone. There's no such feature in iTunes Match
Still not feeling the whole "iTunes Match! Let's manage music on multiple devices thing." ... The iPod was successful, because it was easy!
I can never keep track of which music is where anymore....
What? ALL playlists you have in iTunes are also on your devices. And vice-versa. Match allows ALL devices and computers to stay in sync. Any songs you see on your device with a cloud icon are not (yet) physically on the device. No cloud, it is. You can still have your Recently Added playlist, and it will update on all devices in near real-time. As with any playlist, if you want to have it available offline, scroll to the bottom of the list and Download All.
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And to directly address your concern here, if anything, Match makes things MUCH simpler - there is no longer any managing what music is on what device. Sorry, but it was never easy to pick the 26GB of music that would happen to fit in the free space on my phone. With Match, all that manual syncing and choosing what goes where is no longer necessary.
I get what the OP is saying. If you happen to be somewhere without signal, that's a bad time to realize that the CD you just ripped on your computer is "in the cloud" instead of being available offline on your iDevice. What he's asking is when will Apple have a setting to automatically download all the songs in certain playlists as they are updated. Then you get the automated syncing of your most used and most recent music, plus the availability of the rest of your library wherever there is a network connection. It's a great idea, but they need to iron out the functionality bugs in Match first.
Fair enough, but that doesn't make things any more complicated now than they were before. At least with Match you have the option to stream your content. Either way requires some management if you want to be sure your music is available offline. One requires a computer to sync, the other requires a network connection. I'd be surprised to see Apple offer automatic downloads to playlists any time soon as they are being extremely careful about data usage.
Fair enough, but that doesn't make things any more complicated now than they were before. At least with Match you have the option to stream your content. Either way requires some management if you want to be sure your music is available offline. One requires a computer to sync, the other requires a network connection. I'd be surprised to see Apple offer automatic downloads to playlists any time soon as they are being extremely careful about data usage.
If you want all songs on a particular playlist to be available why not just download them to the devices when connected to wifi, when you create the playlist.
Obviously you have to pick and choose which albums/playlists/songs to keep permanently on the devices. I can easily determine which albums/songs i would like to have with me at all times, everything else is a bonus.
Luckily i have enough space on my iPhone and iPad for my favourite stuff.
If i'm outside cell coverage and i feel like listening to an album i don't have offline, well thats life.