I've been using, playing with, fighting, and otherwise learning iTunes Match since it came out.
Initially it actually worked with very little issue. As I started to work more and more on cleaning up my library (album artwork, song names, artists etc.) I started to realize some of the strange things Match is doing to people.
Its not as intuitive as it needs to be for an Apple product. It feels more like something someone else would have done... but at the same time follows the bloated feel of iTunes.
Having said that, I've found work-around and fixes for each of the hangups I've run into. I've spoken to many who have no issues. I think the few that do label it an Apple failure are going a bit too far, though its natural to believe Apple should hit a home run or not do it at all.
The biggest tips I've learned:
- If things start to not update, disable match in all other machines and devices and concentrate on one. Once that one gets in sync, start up the others.
- Don't try manage music in multiple instance. Do it in once, then use Match on the others to stream.
- If you get in a complete bind, disabling match while holding down the ALT key fixes most if not all issues.
- You can't rely on iTunes to sync. Stop the sync, then do it manually from Store->Update iTunes Match. Works for me 100% of the time.
- Tools like Tune-Up are great, but can conflict and mess with iTunes match (especially as iTunes has been updated, and those tools have not.)
- Deleting from iTunes Match doesn't always work. Do an immediate sync and look for songs to re-appear (sort by iCloud Status, they are easy to spot) - delete these again before they become duplicates.
- There are times when Match isn't working on Apple's side. If you force a sync and it doesn't run, just give it another shot another time.. don't fight it. Come back another day and chances are its going to be just fine.
- I finally just let iTunes manage my library vs. keeping them stored in locations of my choice. I was kidding myself to think I'm ever going to need to get to the .mp3 files again... what am I going to do, buy and old school MP3 player? Or worse, use Android?
- NEVER EVER make hours worth of changes to your library and then sync. Do it in small batches so you don't lose a lot of work in the case things are not syncing right that day. I once spent nearly half a day correctly labeling my 80s music by year (so many get labeled by when a greatest hits came out, not when the original song came out) only to lose all the changes because Apple's servers were acting up that evening.
I have over 17,000 songs in iTunes match, well over 95% are "matched" (and subsequently re-downloaded at 256kbps) and the others are rare concerts and other music I would not expect Apple to every match.
Back up, back up, back up. If you go too long without one and end up messing things up you have nobody to blame but yourself for not taking some precautions.
If iTunes 12 goes with lossless music, I'll be prepared to take advantage of this for the majority of my music. I really hope these rumors are true.
I don't think any other service out there can match Match, even with its quirky struggles. Not in an Apple ecosystem at least, and thats all I care about.