i would go the bikes direct route and ride the stock wheels till they give out and with the savings over name brand stuff I would get a nice set of wheels built. Even if your anti-bikes direct, I would buy a bike from there solely to get the groupset cheap and then buy a frame elsewhere and build it up yourself.

OP, are you looking for something turnkey or would be interested inbuilding something up yourself? NAshbar has cyclocross frames for $100 and with all the discounts that they are constantly having you can probalby get it for closer to $75 and the fork to go with it would be about the same. The satisfaction of building up your own bike is great and quite frankly, if your going to be riding under the conditions you say for a good majority of the time, your going to need to know how to work on your bike unless you don't mind being without it and paying for the LBS to make repairs