I had a wonderful half ton truck. It pulled our 31.5 ft trailer great, handled wonderfully, and everything was perfect.
We decided that we wanted to haul a golf cart which weighs 1000 ish lbs. I knew that I was not going to be able to do this with my half ton. So we bought a dually. 1000 lbs of tongue weight, 600 lbs (at the time, remember they grow quickly) of family... it just wasn't do-able.
We ended up with a dually F350 that I despised.
Had I to do it over again.. I would have kept my half ton and rented a golf cart at the one campground that I really needed to haul it too. (Disney's Fort Wilderness)
My local campground I could have just made two trips with my half ton, one to get the trailer and one to get the golf cart.
The GMC or Chevy 2500 with the 6.0 gas is a nice comfy truck with the same dimensions as the 1500. The Ram 2500 is a nice truck as well and the reports are that its a comfy ride unloaded with respectable empty MPG.
Another option would be to get a NHT trailering package with a GM 1500 and a nice toy hauler. That package should get you close to 2000 lbs of payload on the truck.