How hard on this old of a vehicle will it be to pull a TT of weights within the limit of the vehicle? It has 108000 miles on it as of now and well maintained. Rated at 8000lbs and would stay in the 64...
Towing or not, you're probably going to be putting a transmission in it in about 20-30K miles. Other than that, if the heads haven't cracked by now, you're in good shape for many more miles. The 5.3's in this year range had an issue with cracking heads, but most likely it would have happened by now and it was only on certain castings.