Lurking a bit yesterday due to being swamped with some other issues, sorry.
I am one of the organizers/sponsors/TAs of those workshops with Dan, and I agree, that is also a good avenue to pursue.
(We are planning the next workshop for 11/6 at MIT, and will be continuing to hold them (roughly) quarterly.)
One question is what kind of workshop(s) do we want to have?
The Railsbridge Boston (i.e. Dan Choi and friends) workshop is very much targeted at beginners, and I think given the lead time, we could organize to have a beginner's workshop preceding the conf.
Generally, the Railsbridge workshops are free for participants, staffed by generous volunteers, and only seek sponsors to cover costs (e.g. location & food). If WGRC (wicked good ruby conf) would cover the costs, so we don't have to compete for sponsors for related events, I think Railsbridge Boston could put on a workshop for beginners. We'll have to figure out curriculum, as we usually do a 1.5 day event, but given the lead time, that and other sundry issues seem manageable.
I also think it would be good for this not to be the only workshop, esp. as most WGRC attendees will not be beginners.
I think we should have some mid-range & advanced workshops, like those Thoughtbot has held on TDD, intermediate RoR, etc.