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Was recently discussing some of these iTunes Match "quirks" (and that may be being too nice) on the Maccast. Wondering how many folks are seeing these types of issues and more importantly if anyone has workarounds or fixes?
 
iTunes Match: It Giveth and It Taketh Away

iTunes Match certainly has a few niceties to offer, but I was surprised to learn that you also lose a few features when you take Apple's newest service for a spin. Don't get me wrong, I dig having access to all my music from any iDevice, any Mac, and from Apple TV, and I also appreciate getting higher-fidelity versions of the low bit rate tracks in my library. But iTunes Match unfortunately serves up a few casualties as well:

1. Syncing Play Counts Back to Your iTunes Library. Data junkies will be disappointed to find that, when you listen to music on an iDevice and you later sync that device with iTunes, your iTunes library will no longer update the play counts or the "last played" timestamps. [A]

2. Genius Playlists. Start playing a song, and look at the top of the screen for the familiar genius icon (http://bit.ly/sE7Ze3). Sorry: it's nowhere to be found. [B]

3. Album Art on your iDevice. Though you can see your full library on your iDevice, chances are that you'll only see a small portion of your album art. In my experience, even though all my tracks have album art (and that album art displayed on my iDevices before signing up for iTunes Match), iTunes Match doesn't seem particularly enthusiastic about displaying that album art. [C] Even after giving it ample time to load the artwork for the albums being displayed, it still shows artwork for a sparse selection of tracks/artists/albums. I'd prefer to see the artwork eagerly downloaded; the current implementation definitely degrades the browsing experience.

Here's hoping that these are just shortcomings of a fledgling service, and we can expect them to be addressed in upcoming software updates. The first two appear to be hit or miss, with some people reporting that these features work intermittently for them. If that's the case, it gives one hope that these are just bugs in the current implementation, as opposed to features that Apple has intentionally chosen to leave behind.

[A] https://discussions.apple.com/thread/3495653

[B] http://trick77.com/2011/11/17/no-genius-in-itunes-match-on-iphone-ipad/

[C] https://skitch.com/jasonrudolph/gms9a/sparse-album-art
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Bruce Aguilar's profile photoForrest Tanaka's profile photo
 
I find smart playlists sort of work, but they frequently get out of sync and may or may not get back in sync. For now, I have identical smart and regular playlists, and just periodically copy all the files from the smart playlists to the corresponding regular playlists. Painful.

The iOS 5.0 music player on the iPad sometimes has regular playlists that get out of sync and can't seem to get back in sync. I don't think I've seen this with the iPhone music player.
 
I'm definitely experiencing all of these issues. I don't know of any way to solve them except turning off iTunes Match. Bummer. :-(
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