Wow, thats an insurance angle I had not thought of. Still, not fixing it for a while would save some bread.

I was going to help him work out a couple routes, but I live about fifty miles away so riding with him would be hard.

Taking him on a ride would be a good idea, I may start him on the Frisco highline trail. Its a railtrail fairly close to where he lives.
Good point on the "embarrasment" thing. Sort of admiting to the world that times are kind of tough sucks. Personaly, I would love to live in a city only so that I could ride on pavement to the grocery store.

All I can do is help out if he decides that this is an option.