A guy on Craigslist has a 2008 Fuji Cross Comp for $300. Here's the BikePedia page: bikepedia.com/quickbike/BikeSpecs.aspx?year=2008&brand=Fuji&model=Cross+Comp

I think I can talk him down a bit (blue book value is $255 in excellent condition, for what that's worth), but let's say I can't. I want to use it as a road bike, with some use on the greenways around where I live (which are almost always paved and pretty smooth, with the exception of some rough areas where roots have broken through the pavement).

What do you think? It comes with 30c tires, but if I were to put on something basic like 25c Kenda Kwests, would it be a good road / greenway bike? How much will I hate the direct-pull cantilever brakes?

The other option is a 1996 Raleigh R500 for $250. I think it's way overpriced - at least according to blue book - but I don't know how to read these things. It seems to be in a good shape and mostly original equipment with the exception of cheap plastic pedals. BikePedia page: bikepedia.com/QuickBike/BikeSpecs.aspx?year=1996&brand=Raleigh&model=R500