How does RV Insurance work? How to get around my Catch-22?

Not sure where you live, but here in Georgia we don't have to have a special license to tow or drive a MH. You will have people who try to say that you need a special license to drive over 26K but that only applies to commercial haulers.
Other states may have special rules but look closely at the wording of the statutes in the traffic/licensing codes and make sure you are not mistaking commercial requirements for what you are wanting and intending to drive.