F150 or F250

Nothing against the OP. But I've towed some pretty darned heavy stuff in "half ton" pick ups, over the years. My current trailer grosses out at slightly over 8k and I have no problems towing it everywhere I wish to go. I learned to drive standard shift, at a very early stage, and have towed many miles with one. Now I wouldn't have anything but an auto trans. The one thing I learned was there is a lot more to towing, than connecting to a trailer and hitting the gas. I think that is the reason they put tachometers and give the option to manually select gears. Also temp gauges, rather than lights. All those indicators are there to give warning if you are doing something to the truck it doesn't like.
It may seem that I'm spouting the virtues of the venerable 1/2 ton, and this may be so. But for an inexperienced individual that is towing something heavy with substantial wind load, a larger truck with big payload and larger cooling may be the only answer.