This issue is somewhat near and dear to my heart because I've seen how bad Michigan has gotten. (Partly because of that, I live in D.C. now, and the rent certainly isn't cheap.)
As for the blind leading the blind, how about a teleconferencing link to Boston or Silicon Valley? A company I worked for tried having a couple of webcams/projectors in a meeting room during a Friday social hour to try and link the Connecticut and Houston offices. It only went so far. But maybe if you had an entire wall of an old school "terminal room" style workroom, this could work. Have 3 connected projector/webcam sets linked on a pair of dedicated machines, with software that could quickly and rapidly change functions of the two side screens. (Add some Wiimote hackery for a cheap augmented multi-touch whiteboard, or instant desktop sharing with any machine in the room.)
Hmm, if a rig like this could be scrounged together cheaply enough, one could form a community of such virtually linked hacker-spaces as a network! Maybe use daily round robin, or random pairing. And then, why limit it to just Boston or Silicon Valley? How about Houston-Atlanta for starters?
Future-proofing the standard will take some thought. We would like the standard to grow as technology becomes available, but still be inclusive of older installations.
I also don't think that you hook up with mentors via teleconferencing. For whatever reason, face to face meetings matter a lot. You don't have dinner with someone via a teleconference. You don't tell stories over beer via a teleconference. There's a rigid formality -- "Why are we having this conversation?" I think mentorship rarely happens within those lines.
One of the comments above talks about the face-to-face networking opportunities. There's a reason he didn't say, "Why would I want that? I can call up people via Skype Video now..." ;-)
But I stand by my love for the teleconferencing setup in my house. I'm all over that. (Except, of course, that you're right.)
Well, I don't know about mentoring per se, but if you have an "always on" connection in the workspace, then you leave the situation open for serendipity. What I'm envisioning is just a "serendipity conduit" or maybe "serendipity space." The workspace can become a play-space in the evening or on the weekend. I could even envision communal dinners.
I'm not thinking about people "calling up" other people. I'm thinking of communal spaces with "magic walls."
Why limit it to two? Or, I suppose, if the rig were cheap, you'd just have another room that was Houston today.
I think arts groups like The Field could also benefit from something like this.
Ultimately, enough would stay that they'd influence the local economy. Frankly, any one startup here would influence the economy. It's a small town and hasn't had serious industry since about WWII. Although when my house was built, it was one of the richest towns in this part of the country, and the architecture shows it.
They built cars here. Pianos. Louis Armstrong and Gene Autry recorded here. It was an actual place. It wouldn't take much to make it a place again.
If I was in a different spot, I would probably roll the dice on this endeavor. Alas, I actually have a career.
One other idea for you: Maybe you could hitch your wagon onto the Knight News Challenge somehow? http://www.newschallenge.org/
They just extended their deadline until December, which is plenty of time to build something. And a town like what you're describing seems like it'd be a great testbed for something like that.