I also love the quality of life out here and live frugally, much cheaper than in Boston.
I would not walk, RUN, here from Indy. If you do, there's also a very solid group of Duke Tech entrepreneurs out here that meet regularly.
This is a good point. I'm leaving Indy at some point -- but it is very hard to move from Indy (low cost of living) to SFC or any coast (high cost of living). Especially considering the (current) lack of jobs coming on the market these days.
Given the market, I think the good plan is to either Move there if you know someone to crash with and try to find a job, but if you dont, try to do your own thing and build some resume credibility (read create some web apps or commit some code to something notable) and try again in 6 months.
My cost of living per month is about $2k. It's what you make it. I would try to save up $2k-4k and make the move. If you can't make it happen in 1 or 2 months, make sure you have enough to get a plane ride home.
Either way, good luck.
Funny that you should mention ChaCha because when I got here the most intriguing opportunities I could find were with Scott Jones' companies (founder of ChaCha). I recently started working for SAJE and GalaxiaLighting.com, two of his newer companies, but am holding my judgment until I am there a little longer. I have a feeling I may be on my way out of here when my lease runs up next summer unless something changes. Scott is a serial entrepreneur who is trying to bring the spirit to Indiana through his companies and foundations but progress seems to be slow.