If you want to haul or tow anything substantial, go with a 3500. I drive mine daily, its only as wide as the OEM mirrors, Around town, I let other drivers watch out for the extra Michelins. Plenty of traction in snow, but just like all pickups, need to have weight in the bed to get it. As far as tolls, I too get raped when I leave the Island. %50 of the time the toll collectors don't know any better and charge me like a car, even with the slide-on loaded. The other times, even empty, I pay almost double, one collector says it commercial, other says all commercial over 8k lbs, others say "don't matter, your 8 feet wide", & some say, "what do you usually pay". I owned a trucks before, the best drivabily issue with the DRW's is the stability in turns. Would not consider a 2500 (IMO) for use with a slide-on of any size. Not much choice in tire sizing, but with 860mm's (1998) of rubber in the rear, we have plenty of stopping power when loaded.
Ron