He's got some preferences, but I'm not sure I can find all of them on one bike:
Cranks: he wants two chainrings, and he wants them big (52/50-4?). He's got long, strong legs and he likes to get on and go.
Tires: 700x35 with fenders
Rack mounts would be helpful and he hates drop bars. Price range is $500-700. So far I've found the Raleigh Cadent FT2, but it's new this year and there isn't much info out there and the Novara Big Buzz from REI. Tire size on this one is 700x28 though.
Riding mostly on a rail trail near our apartment, but he might use it to commute to work as well.