Funky driveway = towing concern. Looking for some advice.

I have had the same issue with my old boat trailer. It would scrape on driveways and bend my license plate. I added a couple of small roller fixed casters under the frame. When the trailer would come close to scraping, the wheels would make contact and roll and lift the trailer with the help of the leaf springs. Also had the jack wheel fixed to roll straight ahead to lift front in case of a road bump. Go slow and easy.