I've gone back and forth on whether or not to try iTunes Match and I've decided to go for it.
I have 2 serious concerns; the explicit/clean version issue and the duplicate matching issue.
I've backed up my collection on an external hard drive, so it's there if I need it but I primarily want to listen/create/edit my playlists on my MacBook at home and my PC at work. For $25 it's worth a shot.
I've always cautioned against being an early adopter for anything-Apple, but for $25 I'm going for it.
I'll try to post updates for others on the fence.