3)Is the 3500 DRW truck too rough riding for running errands, sightseeing, and getting groceries? It looks like it will become my daily driver as I can't afford to keep another car if I spend $50K for a diesel truck.
My daily driver since 2005 has been a Ram 3500 dually. Get used to it and it is just fine as long as you don't care for drive thrus or parking garages. Most full timers or mostly timers in the first couple years drive a lot so if towing many places is your agenda the dually probably makes sense. Anything being towed that weighs more than 12,000 pounds would be diesel territory for me.