With the ramp down on the dove tail trailer, there's very little chance of bottoming out when riding on, as long as you're fairly level ground. Truck wheels in a low spot makes for a little less angle.
Going up the ramp seems to bother some people. The first time is the worst, after that it's EZ. Helmet on. Start straight & get up enough steam to get you, up the ramp & onto the flat part of the bed, done deal. I'm 76yo & do it, I know you can. "Back in the day" we would ride our dirt bikes up a 2x10 into a 3/4T. P/U truck bed.