No and No I'm afraid...
First we haven't got space for hosting MP3s. If you want to swap them you'll need to go to a site dedicated for that.
Second Talkawhile doesn't encourage the swapping of bootlegs because it tries hard to respect the artists involved and we don't always know what the artists' views of them are.
This isn't to say we're not, as individuals, interested in bootlegs - many board members are evidentally very interested. It's just that Talkawhile will not be associated with bootleg trading sites.
Generally though, if someone happened to say "I'm listening to a recording of such-and-such" and someone else said "oh really?" a blind eye will probably be turned. What you then get up to with IMs is entirely your own business. Small references from time to time are ok but long discussions on trades will probably be stopped after a while.
As a last word, if someone tried to use Talkawhile to make money from selling bootlegs they'd be slapped very hard!
Hope this makes sense
Cheers
Nick