Although the 1500 as stated above is capable (spec wise) it will depend on the amount of use. Towing a trailer stress's the frame more than not towing a trailer - obviously, so a 1500 frame being less robust than a 2500/3500, the number of miles annually you plan to tow should be your guide (more miles more truck). Additionally power to go is one thing, power to stop is another and the ability of the truck controlling the trailer improves with truck size. With a 1500 your approaching a Tail wagging the Dog scenario on the bad end of the spectrum. Meaning, few if any enclosed trailer loaded weigh lees than the truck pulling them. As the truck capabilities increase so does the sub systems like tires, Wheels, U-joints, transmissions, rear ends. For instance, a dually pulling a 24ft trailer is much easier on everything (truck and driver) than even a 2500 and especially a 1500. But a 3500 dually is not practical for most people. When you go into a curve with a dually it is a much more comfortable feeling than a single rear wheel truck. Aggravate that with a tire typically found on a 1500 and it gets worse. I'm not saying get a 3500 I'm saying think about what your really going to be doing, short trips 25-30 mi a weekend a 1500 should be fine. Traveling 100's of miles regularly get a bigger truck or smaller trailer and enjoy the trip.
As support of my thoughts I've towed using a bunch of methods - Tow bared my first race truck from Roch NY to Reading Pa -320mi, with a /6 stick Van (read as Young and dumb), upgraded to a 21'open trailer and a "Job rated" D150. A D300 Ramp truck, D350 and 3500 and a 36" Enclosed Gooseneck and Now a 3500 and 53' Gooseneck. Of all of those combinations the 3500 and 36' goose was the best (all things considered). I am now in the midst of getting a bigger truck, The 3500 pulls the 53" but very close to the "Tail Wagging the Dog" scenario I spoke of prior. There's my
make of it what you will.