Besides weight it depends on what you're hauling....people, hazmat, etc.,. We've always ran less that 26k...straight box trucks and pickups...we basically had to do everything that CDL drivers/trucks do...except have a CDL license. We had to have trucks inspected, proper tags, DOT emblems, logbooks, health cards, etc.,....but only a regular driver's license required...no CDL.
We never pulled trailers, though, so I would definitely inquire about that...I'm thinking you will be required to have a CDL being as the gross combined weight of the tractor and trailer (the unit) will exceed 26k gvw.
Warning: Rookie beek...take my postings with that grain of salt you keep in your pocket.