Chris S. and I had a meeting last night with two transportation planning consultants who are interested in the work "we" are doing. ("we" because Chris singlehandedly did all of the
famous stuff and I'm mostly just coattailing at this point). We talked for a long time, and they eventually gave us a bunch of data and a free server, and one of them seemed interested in recruiting me into transportation consulting, which is basically all I've ever wanted to do. I'd jump on it, but I'm not certain that I'd want to abandon the security of a nine-to-five job while I still have so much debt. Chris, by contrast, is pretty fantastically hire-able, but he's working at Amazon likely making more money than God, so he's out of the rat race for now.
There is an interesting catch-22 in making GIS-enabled internet application with municipal data: Anyone who can actually finish a cool GIS project is totally hot and can scoop up huge amounts of government GIS project money. By taking government GIS project money, however, you doom your project to bureaucracy and sloth, and will no longer actually be capable of doing cool things. It's like when MGM bought out Buster Keaton because he was a ninja, which effectively extinguished his ninjahood.