Over the last couple of days I have been slogging through iTunes Match with mostly good results, but not universally good results.  First a couple of observations:

• With over 16,000 "songs" it took a couple of days for iTunes Match to match my music. During the process, what was going on wasn’t clear.
• iTunes crashes on the Mac as it tries to sync iTunes purchases from the iPad.  Seems to be associated with video, but not clear.

Problems:

• Biggest issue: legitimate songs, which I have owned multiple times (like Fool on a Hill on the Beatle’s Magical Mystery Tour– I have owned this on 45, Cassette, LP and CD) didn’t match. The rest of the album did. I have this in several places. I get the obscure music that was an extra on a CD version that Apple doesn’t have or an old, "I’m not sure where it came from" version of Bowie’s Space Oddity (better known as: The Major Tom Song.)  I’m guessing that the matching technology
• Low-bit rates: as promised, low-bit rate songs, like an ancient MP3 of Elvis 56 with bit rates in the double-digits (like 82 kbps) didn’t load. That is OK, but it would be cool if it provided an analysis that let me
• Re-ripping requires management. I still have all my CDs. Where I found an issue with a CD (like one song had too low a bit rate) I re-ripped the entire album at 256 kbps. Because I have used many programs to rip CDs in the past, the metadata isn’t consistent. Even though iTunes knew I already had the CD, it didn’t overwrite all of the songs, just the ones that matched exactly, and then it added the no-matched songs as new, with different metadata (most notably track numbers like "1 of 13" where the original was just a "1"). That meant that, for those song, I had to rename, delete from the collection and the cloud and then make sure the playlists were repaired. You can see what playlist individual songs are in, but there isn’t an automated way of saying: "replace this song in playlists with this song". So this playlist management remains manual.

What’s missing:

• The state of your collection. Isn’t on by default. If you want to see you have to expose the "Cloud Status" field. This is useful, but not overly informational as I can now see my Beatles turned were uploaded but not matched, but I’m not sure what to do about it.
• Analytics: Apple is missing a marketing opportunity, or perhaps they just haven’t unleashed it yet, to reach out on old music and suggest you buy the higher quality version. It may be they don’t have the song exactly the way you have it (say an old greatest hits CD) but they do have it in some form that is close (likely, the songs are exactly the same, it just the album that is different).  I’d also like to see charts and graphs that tell me how much of my music was matched and tools to help me figure out how to fix stuff I know should match. Again, the entire Beatles catalog is on iTunes. Every song should match.
• Attention to Spoken Word. I have all of Shakespeare’s plays and several volumes of poetry being read. Apple is about music and books on tape and these aren’t really either, so they aren’t handled very well.  I would like to see a category for Spoken Work or perhaps just exclusions in general that, like Audiobooks, is taken out of the music match process, making the results more meaningful.
• A match challenge: if iTunes Match can’t find a song, perhaps iTune should have a process where it presents you with a list of song it thinks could probably (us pattern matching to go to present only high probability matches) and let the music owner fix some of the match errors that turned into upload. I’ll go back to Magical Mystery Tour. If iTunes Match can find the album, another pass should show I have a song called "Fool on a Hill" that is a 98% match for the iTunes version. Let me confirm so I can match vs. upload. In the end, it may take time, but the consumer wins with higher quality music and Apple can save some server farm real estate.

What’ Cool:

• I deleted my entire library from my Mac. It wasn’t very big as it was just a few copies of songs I wanted to sync to the iPad copied over from my PC. With iTunes Match, I now, for the most part, get high quality versions of matched songs on the Mac library as I choose to listen or download them. Of course, the ones on the iPad and the iPhone are also higher quality now, but you can’t really tell (would love to tap and hold on a song at at least get some basic metadata about it on the iPad).

As I go through my collection and try to clean-it up, I’ll update this post to share other experiences.

What have your experiences been with iTunes Match?