Well iTunes Match will be $25 a year. That might include storage for the uploaded tracks.
Good point, maybe that will be enough to cover the additional storage. But my guess is that a lot of that money will go into the music labels pockets. They wouldn't have agreed to this unless they thought that they would make loads of money from it. I hope I'm wrong. I hope you can upload bootlegs. It would be very useful if you could.
It's an interesting question from a legal perspective as well, since some bands are very encouraging of bootleg recording/sharing, and some are against it. So I'm not sure how Apple will manage that problem
Unfortunately, the one thing we know about Apple is that if someone thinks that they have even the slightest chance of a claim against them, they sue.
On a side note, I wish that more bands sold their bootlegs on itunes. A lot of big bands now have official bootleg programs, but I've only ever seen a handful of them on itunes. I doubt we'll see it anytime soon though, since they won't want to give up a cut to apple [even if they would be reaching a larger audience by doing so].