Beginner 2014 Dodge Grand Caravan

I would not want to pull a hard side TT with a Caravan. The high profile of a TT means wind will push it HARD, which will want to move the tow vehicle around. Sometimes it will succeed, and the tail will wag the dog. A minivan is built to deliver a nice smooth ride, so it has a soft suspension and squishy passenger car tires, which means less than optimal control in crosswinds and on rough roads. You'd also be right on the edge of your weight limits, if not over. Even if you didn't toast the transmission--a distinct possibility--you'd have a white knuckle towing experience. Towing overweight or with a marginal vehicle is no fun. Been there, done that.

I would stick with a popup. The larger ones have A/C, slideouts, etc, and can easily sleep five, while still being well within the capabilities of the Grand Caravan.