We used to have a 28' TT that I towed with an '02 Chevy 8.1 short bed. Worked out OK, but it was a lot of work. (Loved the truck though!) When LOML said she wanted a 5er, I started shopping for a new truck since pulling anything the size (34'-40') she liked was out of the question with the Chevy. She was still not totally happy with anything when I found the truck that would work no matter what she settled on. Older, but only 28k miles and in great shape. She picked out our Montana, but we both agreed on it. After about 30k miles of towing in three years (and I've got to do all the driving), I couldn't be more pleased with the truck.
Our first trip was from VA to MI and Canada, and I could easily drive 300+ miles a day without being worn out at the end (and I was 69 on that one). The next year went to NM and AZ through heavy cross winds that I could hardly feel. Last year was through NB to San Francisco and back, ditto the cross winds. This year we're going to Montreal & Quebec City (a short trip break). Even with your smaller trailer, you'll never regret having a decent tow vehicle!
'06 F350 TD, Softopper, airbags, AeroShield, coolant filter
'10 3665RE Hickory edition, wetbolts, Firestone LTs, Trimetric Battery Monitor, 4x100w panels & Morningstar TS-45, still tweeking.