I will actually answer your question: Yes we had two TT, a 24 Ft and then a 30 Ft before we upgraded to a 5er. Pulled both TTs with a 1500 Chevy long bed, it did the job but after a long days travel I was beat.
Up graded to a 3500 Dually (got a better deal than ordering a 2500) in prep for a 5er. Now it handled the TT with ease and now where as beat at the end of a days travel. Then came the 5er, BIG difference in towing and handling, but a learning curve in backing.
But now would never go back to a TT after towing close to 100K miles with a 5er.