Others here can address things like lift kits, 4WD, bigger tires, etc. I can only point out that given the same undercarriage clearance, a shorter wheelbase will reduce the chances you will bottom out. We could not buy the 170" wheelbase Sprinter because we could not get it into our sloped driveway - the angle changing from the road to the driveway was so great, the van would center in the middle of the transition. The 144" wheelbase on the Transit (and anything shorter) would handle it just fine.
2018 Coachmen Crossfit/Beyond