I dont know your area but I know about towing a 30 footer ,
If you use your boat few times a yea, storage at home , operating like a camper , and have able hands too assist , then NO BIG DEAL
Towing a smaller boat ( lets say a 21 footer) your still faced with operating condition of trailer , truck , , brakes , tires
But once towing a large boat / trailer/ tow truck , everything changes ,
Proper tow vehicle a must , good tires , brakes , same with condition of trailer ,
Your over 50 ft down the highway , Your like a small tractor trailer ,
Most don't have the experience handling equipment that long , wide, going 50 mph down the highway
IT BECOMES A JOB , At times white knuckling over windy bridges , ,
Former truck driver , 30 plus years , I have a sense that others don't ( u truck drivers know what I mean ) but the idiots still scare the hell out of me ,
If anything happens accident wise , and they find your vehicle or trailer had issues , financially your life can change instantly ,
Always owing some sort of boat , majority of the time towing
Years ago purchased a 30 ft cruiser , It was sitting on a 3 axle disk brake trailer ,
Boat is 9.5 beam ,
9000 lbs
Trailer rated 15200
My tow vehicle is a older work F 350 , Gas , 5.8 engine , Truck is a beast , rated 11500
8 ft beam no permit
under 9.5 a yearly blanket permit ( here in Florida ) $ 25.00 , ( beats DOT pull over ) $ 1000 dollar fine
9.6 & wider permit costly , and don't know if you fall under escort
Better make sure your vehicle can pull you up ramps ,
My beast has no 4/4 , most ramps I get out ,
9000 lbs from a stop up a steep hill you need a strong truck ,
Steep ramps I don't have enough torque , rear wheels spin , as a precaution I ride with 100 gallon empty ( rusted not used ) gas tank that I fill with water , Gives me 800 lbs over rear wheels , helps , .
I also use boat weekly , since its such a hassle I leave in a wet slip , Not fond about marina fees , but once over
a certain footage you fall into yacht category and everything changes ,