I know what I did to my 1997 F150 when it had around 70,000 miles on it and I just bought a #5000 TT about 11 years ago..
Most of what I did gets a big "poo-poo" here and many other boards, but that's fine... ;)
What you need to do is find mods that keep or increase torque in the lower rpm range.
I went with the option to feed the large air pump more air.. I didn't swap gears and I'm running 3.55's with a LT265/75/16 tire!
I did it with an exhaust mod and an air filter mod.. For the exhaust, I went with a aftermarket 3" 'cat back' setup. Get the muffler of your choice for the kind of sound you are interested in. I got a straight thru style, yet it does not drone you out of the cab, but it does provide that nice V8 sound I do love to hear... :)
For the air filter, lets just say it's not a very popular brand on this site and others.... I've not had the issues that's always stated with the use of this type of filter, but that's just my opinion and experience and I'm not saying the other folks didn't have issues... I just have not been one of them..
That being said, my F150 now has 246,000 miles on it. I tow the same #5000 GVWR TT from 11 years ago and I'm still running the same cat back exhaust and air filter.
When I first got my TT, I had the cat back and air filter, but the original muffler that came with the cat back was essentially a POS baffle type of muffler that really didn't live up to it's hype.. But, it was better than the OEM muffler it replaced... ;)
When towing with the POS muffler, I could not hold OD for nothing... It would downshift on any rise in the road (over passes for example). I was so close to doing the gear swap at this point....
But, the POS muffler developed a rattle and I replaced it with the straight thru muffler it still has to this day.
The first tow over the SAME route with just the new muffler allowed me to run OD when the conditions were right. It did NOT downshift on every rise in the road. I got about 1-2 mpgs better towing (I get around 10 mpg now) and the truck drove and had a lot better throttle response all the way around..
I know I have no 'proof' of this and I'll be called out on it, as it is just my own seat - O - the pants meter and my own performance comparisons I'm going by...
But, I know what I had and I know what I have and even when I have to swap out my air filter for a paper one when it's being cleaned, I can tell a difference with just a different air filter... Yes, I'll be called out on that too, but again, it's just my own SOTP feel and I can't prove any of it... ;)
Maybe it's all my own perceptions or false feelings because I spent money for the mods and really 'want' them to make a difference?? Dunno, but whatever, the results for me was positive and I'm happy, so there you go!
I'm not saying you will get the same results.... I'm just saying what worked for me...
Good luck!
Mitch