Noles,
What is the aprox dry weight of your current tt? Asking to get a rough cargo weight?
What do you haul in the bed when you head out? Aprox weight? Any accessories added to the truck, like a topper?
Aprox family/ passenger weight in the truck?
As mentioned, I would be surprised if you are under your trucks payload. What is the amount listed on the drivers door jamb sticker?
Best bet is to go for a 2500/3500. A 3500 isn't much different price wise and you have even more payload availabke if you decide to go with an even bigger trailer later on down the road.