I have never towed that long. I have heard, that those longer TT can have issues with gusty winds, but you do have a capable truck. Personally, I would be okay driving that set-up, and I have a little 21' TT right now. Pack it decent, correct tongue weight, good WDH, slow down in windy conditions, and I think you would be fine. Only you know your confidence level, it's not going to be a big deal most of the time, but that said, it is a long set-up and takes a driver that is aware of their surroundings. Some are, some aren't. If you are a fairly confident driver, I think you'll be fine after a few days under your belt. Hopefully some others with experience chime in