We used to tow a 20' TT with a 1/2 ton. Easey peasey including in and out of tight mall parking lots.
Have towed a 29' TT with an F250 with super cab and long box for 3 seasons now. No issues with gas stations or CGs for length. Stopping for groceries on the way to a CG can be a challenge sometimes to find a parking spot. Always use your assistant as a spotter when backing up. With a longer wheelbase truck, I've found that right hand turns at 4-way intersections are harder to get around and you have to pay more attention to executing the turn without hitting a curb.
One of the most important things if towing a longer and heavier TT is to have a good WDH and sway control and have it set up properly, especially if towing in hilly areas with roads with lots of twists and turns. We have a Reese dual cam WDH and it is awesome. It has taken a lot of fiddling to get it adjusted properly, but this is "normal" for these. We just drove hwy 299 from Redding to the Cali. coast and I can't imagine a more challenging road for twists and turns and elevation change much of the driving at 60 or so mph. The TT and TV combo handling is excellent. The only hitches that would be better are a Hensley, Propride or maybe Pullrite but cost a lot more.
We added shocks to our TT and HD Bilsteins to the truck which have helped a LOT for handling and stability. Sounds like for a TV you want at least a 3/4 T.