I've done the multiple gigs thing, and I'll do it again if the gigs are right. In this case, they are 2 hours apart and 2 hours of driving (if there's no traffic) distance. Just not a good idea to try to do them both - the likelihood of some variant of Murphy's Law taking effect are too high.
I'm still bummed, though - both are gigs that would be fun.
The one we're doing (booked first) - my first gig with Funkranomicon.
The one I can't do - benefit gig for BadRap (pit bull rescue organization in SF).
www.badrap.org