I just scanned this post so not sure if this has been mentioned, but one problem towing that heavy of a TT with a 1/2 ton is that the running gear components wear out a lot quicker. I'm towing with a 1/2 ton '94 k-1500 Suburban. Bought it about 2 years ago. Was a one owner, always garaged 130,000 mile cream puff. Good and complete maintenance records. It was never used to tow although it has the tow package and all the options. After towing for those 2 years and about 10,000 miles the rear pumpkin began making noise and had to have the rear bearings and seals replaced, then the front diff started making noise and had to have the same repair. The well experienced mechanic said the differentials would probably have lasted almost forever, but the towing took them out as they were not heavy duty. Our TT is only about 5500 lbs loaded so it was well within capacities. So bypass the 1500 and get the 2500 ton and save money in the long run (not a Ford fan so bypass the F150 too).
My son had a similar thing happen to his 1/2 ton '05 Dodge Hemi, and his trailer is lighter than mine. We towed for several years with a '88 3/4 ton 454 Suburban and never had a single running gear problem.
