1994 Ford F-150
Clyde,
You said the engine was a straight-six and called it a 4.9L. I used to buy E-150 vans with what was called the "300 six", is that the same engine? (Before the 300 they used to be 240's) Damn engines were bullet proof! I knew a company that bought one brand new and never changed the oil for 96,000 miles! That's right, never! All they ever did was add a quart every now and again and it ran that long before sludge plugged it up and it coughed it's cookies.. That is the only 300-six I ever heard of that died.
My vans were loaded to the point that every once and a while I'd break a leaf-spring in one of them. I have no idea what they hauled for weight, but I'd say a two-ton trailer shouldn't tax that engine too badly.
Back in 2003 I had an '99 F150 with the 5.4L V8 (the previous one had a 4.6L V-8). It had been my company truck and I bought it from the company for personal use as Becky and I decided to take a two-year sabbatical and tour the USA and Canada with a 23' tow-behind trailer. That truck had 125,000 miles on it before we left on that trip. I had been reading RV mags about people having transmission problems with tow vehicles. (Mostly Dodges.) And I got to wondering how my tranny would do with long term towing, so I installed a transmission temperature gauge. That gauge never budged off the pin until we were way out West in 2004 going up over a 12,000-foot pass. Then it went up to 230 degrees F, but came right back down after we started down the other side. We covered 46,000 miles over 18 months on that trip and when we finally sold that truck it had 210,000 miles and everything worked except for the A/C, the bearings were gone in the compressor.
I don't remember, but in your detailed list, did you specify how many miles were on the odometer?
By the way, I currently own a Hyundai Santa Fe Sport with a non-turbo 2.4L four-banger in it. It currently has 70,000 miles on it and I tow a one-ton boat&trailer well over 3,000 miles with it every year. ( I don't want to hear any crap about owing a Korean car either! The engine and transmission were both manufactured in the US and the vehicle was assembled in Georgia!)
You live in FL which is pretty much flat, unless you live in "Mount" Dora where "huge" hills soar to 184-feet above sea-level! I don't think that will tax your tranny too much! (Especially with all the fancy extras you've added.)
I'd say, "Tow Away!!"
Rog