First, I don't think of myself as a random potential idiot, but I get your point. Second, I do have plenty of towing experience including TT and 5th wheels. I just don't currently own one. I owned a 19' Aerolite TT that I pulled with my 02 Dodge Dakota 4.7 for thousands of miles. No problems at all. But kids got bigger and busier and didn't leave much time for camping so we sold it. I've also towed my dad's 5th wheel with his F250. To me I didn't notice a huge difference in towing experience between the two setups. The TT was setup correctly with an Equal-i-zer hitch and handled well.
Also my current F150 is a work truck. I'm half owner of an engineering firm and we both purchased new vehicles through the company 5 years ago after a really good year. He wanted an Expedition and I wanted a truck. So since the company owns it, selling it won't be as straightforward as if I owned it directly. An upside is we have great insurance if I ever go careening down a mountainside and kill thousands of innocent puppies! I will check to make sure I would be covered pulling a TT for personal reasons though. I use it as my personal vehicle and get imputed income on my W2 for personal miles.
Since it is a work truck, I have used it as such for field work. I've packed the bed full of field gear (ice chests, generators, etc.), loaded the cab full of guys and gear, plus towed our 5x10 single-axle cargo trailer that we tend to load tongue heavy. Thinking back, I bet I was easily 300 lbs over GVWR in those scenarios without even noticing. No issues then at all.
I do have a family friend (father of my daughter's boyfriend who practically lives at my house!) that just bought a
Grey Wolf 26DBH. It's heavier than what I'm looking at by about 1,000 lbs, but he tows it with his half ton Chevy. Maybe he'll let me hook it up to my truck and take it to the scales to see how it handles.
Thanks for all of your replies. Certainly has made me think about all my options.