I have towed my trailer with both half and three-quarter ton trucks in Michigan.
I was at half-ton ratings with nobody in truck, and this is how I hauled it about 50 miles max. It did fine. I did not want to haul daughters and dogs with the half-ton.
The three-quarter is my wife's daily driver. She has learned to park where it is easier to park. That is really the only down-side to the 2500.
I would recommend that you start with the 2500, and go with the larger tow vehicle and adapt to in the daily driving habits.
