Any of the 3500/350 trucks will handle your trailer, particularly with a diesel up front. SRW is plenty for occassional towing (or for some of us, frequent towing; but that is a purely personal decision based on experience).
DRW would really be overkill for the situation you propose. If later you decide to do more traveling with the trailer, that may be a different option.
There is far more difference in ride (particularly when running solo) between a long bed and a short bed than between SRW and DRW. The extra wheelbase takes a lot of the chop out of the ride. Again, it is personal opinion, but having driven all three I feel that GMC/Chevy trucks have an inherently more comfortable ride. (They also have Duramax/Allison.)
