Having issues posting so no quotes, but responding to lawnspecialties.
This is a big part of it. My FIL owns an oil field hot shot company, towing very heavy gooseneck flatbed trailers (Big Tex and the like). Before that he worked in the oil fields driving their trucks/trailers. After a scary trip with our trailer, when we had the F150, he brought it back for us, along I-80 in Wyoming where it's very windy, with it just attached by the ball.... no WDH, sway bars, or anything. It was with a 2500 truck, so a difference there, but he drove it like it was nothing. Even when we had a 250, my husband was still pretty nervous, which then made me nervous, which then made for a stressful trip. Only now with the dually that he feels pretty comfortable towing our trailer, and TBH, that's one of the reasons we're going to upgrade to a 5th wheel, because they are easier to pull.
So yeah, someone should take into account their own experience when deciding what truck/trailer to buy. We learned our lesson and should have bought the bigger truck to start.