TMAC, my truck is a 3/4 ton with Cummins, but I don't think you would have to have that for transporting up to 50 miles and only once per month. I'd say you definitely want to get an 18 ft trailer with brakes on one axle (the front axle) and air-lift shocks for your truck. The 1/2 ton suspension will really "squat" in the rear if you don't have a load levelling device or air shocks you can air up as needed. I used to have air shocks on a 1/2 ton GMC and it was fine for the once-in-a-while hauling. Even my 3/4 ton feels the tongue weight with both a loader and rotary cutter attached to the tractor. I'd never consider hauling loader, tractor, and rotary cutter at the same time on a 16 ft trailer since the cutter would hang off about 4'.