Hey folks! Sorry for the slow reply, but I'd be happy to help put things together in Boston.
I suspect that we won't have too much trouble finding a venue. There are a number of hackerspaces in Boston and Cambridge (which is right across the river), and I bet one might be willing to help us out. hack/reduce, in particular, has a great space and location and often hosts events. They might even host us gratis, if we're lucky. If we're committed to Boston, I'd be happy to ping them about it.
Funding for food might be a little trickier. My employer, thoughtbot, sponsors the Emacs meetups in NYC and Boston, and they might be able to chip in for food and some miscellaneous expenses. They've also helped with video editing and production. I'll sniff around and see what they'd be willing to do.
The FSF is pretty good at putting together a conference (LibrePlanet was this weekend, and it went very smoothly), so I definitely agree that we should try to get them involved. They could probably help us with finding venues and sponsorship, and I'd sure like to have RMS come talk.
Personally, the ideal weekends for me would be July 16-17, Aug 6-7, or Aug 20-21.
@tzz: Hi! If you're near Boston, we'd love to have you swing by EmacsBoston some time! In fact, there's a meetup this very evening!