40 pounds is a lot to haul for a commute, and the first thing I would do is try to cut that down. If that's not a possibility (or even if it is), depending on where you are located, $250 may well be enough to buy you a decent vintage touring bike, which would probably have: 1)the ability to hold all of your crap with front and rear racks, 2) low enough gearing to get you + your 40 pounds of cargo uphill, and 3) enough room for nice sized, comfy tires + fenders. Schwinn Voyageur/Passage, Trek 520/620/720, Miyata 210/610/1000, plenty of other brands. Look for lugs, cantilever brakes, rack/fender mounts on the fork and dropouts. My 2 cents, anyway.