How much trouble do you think I'll have getting around with, say, a 31-ft. TT, pulled by a 2002 Chevy Silverado 2500HD with a crew cab? I'm looking at a 31-footer that I might want to buy.
Many state parks in the Pacific Northwest will be troublesome with a trailer over 26' which is why we stayed with a shorter combination. If you boondock, the longer trailer may bottom more often on uneven terrain unless lifted.
Your vehicle will not have trouble towing it, you just need to make sure the places you want to go will fit it.