i don't see any problem, a large majority of the car haulers out there with day cabs have the provision to carry one and sometimes two vehicles on the tractor in that fashion. that rig definitely isn't even blinking at the weight.
the only possible concern would be if you had a really lifted/tall vehicle. most trailers (and most modern tractors with sleepers/fairings) are 13'6", so even the pictured combo with the jeep has plenty of room to spare before exceeding that. even going taller wouldn't be an issue assuming you obtain an overheight permit and were careful of your route away from interstates.
there are some exceptions out there, especially on older sections in the east, but pretty much all interstate overpasses have a minimum clearance of 16ft. (plus a few inches to allow for resurfacing) as required by current regulations. that clearance must be maintained across the entire road surface in rural areas. urban areas only require it in at least one lane with any remainder being no less than 14ft. u.s. highways, state routes, and surface roads are a different story...