I wonder if you might be able to find some info over on the Escapees MDT forum? Sorry I don't have any knowledge of Indiana law. In Minnesota you would need a Class B license to drive it. A standard Class D license (in MN that is) only allows you to drive a vehicle up to 26k lbs. And only allows you to tow a 10k lbs. trailer. Unless said trailer is a recreational vehicle, then there is no weight limit. I would guess Indiana is going to be quite similar. What about the possibility of down rating the weight on that truck?
MDT - Escapees Discussion Forum
'03 Freightliner FL112, 295" wheel base, with '03 United Specialties 26' living quarters, single screw, Cat C12 430 h/p 1650 torque, Eaton 10speed , 3.42 rear axle ratio