Would I ever be happy towing with a half ton truck

I actually plan on going to a so-called 1/2T.
My TT maxes out at about 9400# and when I replace my truck, I want to use one of the new Diesels. At this point they're evolution is not where I want them to be but they are getting closer with every model year.
I look forward to the better fuel efficiency, ride and overall comfort of the "lighter" truck.

For 8500# it would be really close. If you don't tow over mountain passes all the time like I do, I think a properly equiped 1/2T would do fine.