I've been playing around with iTunes Match, and while there are some things I really like about the concept, I think it really isn't for me. I have a large library (24269 songs, whew just under the limit!), 22402 of which are lossless encodes from CD. I have spent years organizing and getting my metadata and artwork just like I like it. I don't mind that the lossless files are converted to 256k on upload, but what bothers me most is that I can't control what a file is matched to. It has already been mentioned about songs from the Beatles Mono box set being matched to stereo versions. I am finding similar problems with matching being confused about alternate mixes and remasters. What would make it much better for me is to have a simple option of "Force upload to iTunes Match" for a song. That would make iTunes upload my version of the song to the cloud no matter what iTunes thinks it might match. Maybe I'm a control freak when it comes to my music library, but I can't switch to using this if I can't get the song I want to my device.