Funky driveway = towing concern. Looking for some advice.

My trailer is 24 feet long and the hitch is 23" off the ground when level. It easily manages the kind of terrain in you photos. Coming in at angles while paying attention to low points like the black/gray drain is all there is to it. I personally don't see a problem with flipping axles if it's needed, but there are plenty of trailers out there that are already high enough. Looks like a fun location. Good luck!