Once iTunes was done and I had surveyed the destruction I had items that when you try to play them you receive “this item could not be downloaded” error. What you have are items iTunes thinks are in the Cloud but are actually broken in the iTunes&Cloud; database (a db entry without data. that’s my take at least).
*To finally (make iTunes stop crashing) finish iTunes Match I had to run ProcMon from SysInternals and track file open operations until I found the songs iTunes was choking on each time it crashed. In my case it turned out to be a couple of old items that were 100+MB… Who knows… I’ve dumped a lot of random crap in iTunes over the years. I got the idea for this procmon fix from user posts on the Apple Support forums, thanks guys!
Once past iTunes poor error handling iTunes Match decided it had completed (and I use this bitterly). I came to find I have a hundreds or more songs that are broken in the cloud and iTunes. I may still have more that I don’t know about.. However, I did not yet know this…. I decided to delete some songs indicated as successfully Matched and try re-downloading them to verify iTunes had worked. Oops, nope, it just thinks it worked. When iTunes crashed it thought it had uploaded them to the cloud but it had not. How does this get past Quality Assurance guys?? Hire a few more Testers and think of it as a stimulus…but I digress.
Well now those songs are broken and in iTunes limbo… I wanted those suckers back/fixed. To be fair I had 24k songs purchased or backed up over 15+ years in a variety of formats. I decided to fight through the pain and fix the broken items in iTunes because, well, this is my Music collection dammit.. So this is one method of recovery…
*If this doesn’t work then you might try deleting the song from iTunes and re-adding the restored item.
**This works 98% of the time for me.
PS – Here’s the part that sucks. The Song is fixed in iTunes on your computer but it is not fixed in the cloud. Once again iTunes Match is stupid. If you delete the song locally you will still receive an error when trying to download it from the cloud. I don’t know how to fix the “cloud” yet. Apple.. help? Anyone?
Quick Update ( iTunes 10.6.3)
As of iTunes 10.6.3 it appears the issues I was encountering with broken songs have been resolved. I can now download the broken songs however Itunes does seem to sit and “sync” my library indefinitely. It started with the lighting bolt next to “Music” so I clicked it and have allowed it to sync with the animated cloud symbol next to “Music” for 7 days now.