as far as TT size i think you will be comfortable towing that size TT. our first TT was 33ft and loaded to camp was in the 7500lb range. our current TT is 37ft long and approx 9500lb loaded to camp.
my truck is a 2017 f250 6.2 gasser with 3.73 rear end.
wdh and sway bar.
the truck has towed from nc to niagara falls, florida, mountains, and coasts and everywhere inbetween. we have a 37ft TT because wife wanted 3 slides and more space. a fifth wheel with 3 slides would push my truck to the max and i prefer a comfortable towing experience
your TT length shouldn't give you any problems at gas stations. mine does so i plan ahead for fuel stops at gas stations with plenty of space.
gotta watch the curbs closely when turning but overall im happy with the setup
enjoy!