Worries about clearances

Measure the distance from truck rear axle to trailer front axle. Measure the clearance from the lowest projection to the ground... probably around the hitch. Cut a board to the length between axles, lay it over the hump, push one end to the ground, measure the distance between the board and ground on the other end. If it's greater than 2X the clearance - don't try it! That's also called the breakover angle. I've done it with string - drove a fire truck for a bunch of years - it's called preplanning, know your roads!

You can gain an inch or two by approaching at an angle normally.