My 2 cents: I was looking at similar bikes a month or two ago, and really liked the Fuji Cross 1.5 disc (posted about it in another thread). It runs about $100 more than the crossrip comp disc, but has 2x10 tiagra fd/rd/brifters. Anyway, I rode both of these bikes and really liked the Fuji. Nothing wrong with the Trek certainly, and it might even have a higher resale value than the Fuji due to the name recognition (I can't comment about reliability since I didn't end up buying either bike). As far as the upgrades, my research into bikes has told me (1) upgrades are expensive and (2) just about every config you could want is being made by somebody. So if I were you I'd look for something that's more "ready to roll" right off the shelf...if you're sold on the Crossrip Comp, maybe check out the Crossrip Elite?