I have 21482 songs.
"Its a lot of punk and ska and some show tunes or whatever"
(actually its a lot of alternative, underground hiphop, indie, prog rock, ska(all waves), and spanish stuff)
I'll be using yousendit, the files are mostly mp3, some ACC: no wav or wma.
EDIT this is going to take all week as all the music is on a 400mhz computer (and you try uploading and messing with itunes on an old g4!)