While I have what most would consider a short trailer 21' tip to stern, I had similar concerns with my driveway onto the highway from the crown of the road and driveway and the gutter dip. Better clearance pulling in than out. I recently had my axle underslung on the springs from over. Just that gained me 5&1/4" clearance (best I can measure). But before that I did not install my WDH spring bars until after leaving my driveway to keep the TV to TT better able to pivot at that dip. Do you back in with the WDH spring bars connected?