My F250 looks just like the F350 in Daveplot's post. Pretty, huh.
I have a lot of experience towing a Jeep and trailer, so I'll give you an honest breakdown here. I have towed with the following vehicles with the same Jeep and trailer: 99 Silverado 1500 with 4.8L 2WD, 00 F150 with 5.4L 2WD, 97 Suburban 1500 5.7L 4WD, 05 F250 Powerstroke 4WD.
The Silverado was the worst of them obviously, but still got the job done. The engine did well, but the rear was light making for scary stops. The F150 pulled impressively for a small block, but drank gas like it was "last call." The Suburban was slow and steady, but scary as hell to stop even with trailer brakes. It needed 3/4 ton disk brakes. Finally and really not a comparison is the mack daddy F250 diesel. It will change your life. I can run 80-85 comfortably down the highway with the Jeep and trailer. It doesn't bog going uphill, can support all the tongue weight you want to give it and the best thing is that you feel in complete control over the trailer. No pucker factor whatsoever. The integrated trailer brakes in addition to the monster 13" disc brakes make it the King for hauling. I have to disagree with Sparky on the F350. The only reason to go 350 is if you need a dually. The tow ratings aren't that different. In fact the only difference I have seen is the rear springs. Axles and drivetrain are the same.
What it boils down to is how heavy is your Jeep and trailer and how often are you going to tow it. Twice a year, I would go with the F150. Once a month, would be the F250 for sure. Remember, trailer brakes = good.