It wouldn't need to be licensed (other than a regular tag) if he only towed his own cars and didn't hire it out.
The truck is tagged and street legal, but I don't tow with it other than around my property.
Here's a picture of me moving a 30' grain trailer that I sold a few years ago. I had to move it up to the street so it could be loaded on a lowboy trailer that was hauling it to Canada.
Mike B
Mike Boteler
1956 Chevy 3100 Resto Rod 1952 Willys M38 Army Jeep 1983 Jeep CJ7 Laredo 1984 Jeep CJ7 +++++ Silver Spring, MD