Have an acquaintance that has a motorcycle race team. He owns and uses a full sized, conventional semi as his transport. He has no CDL because he was able to get the proper paperwork stating that his semi is classified as an RV. Also, he doesn't go across any scales. I am pretty sure he has "Not for Hire" on the truck cab.
Something maybe you or somebody else might look in to when thinking about a rig that size.
Some states are starting to crack down on the "RV conversion" of big rigs, especially if they are used for questionable purposes. Pulling a race trailer falls into that category since there might be prize money involved. The reasoning is that if you make a single dollar, then you are in commerce, thus requiring all the licenses and fees required for a commercial truck.
I was told by the Idaho DMV that I could drive and pull any vehicle as long as it was mine and wasn't used to make money.