OK here goes my 2 cents worth. I used to live in St Louis and sail a C22 on Carlyle lake. Four times a year I would trailer it down to the Keys to sail. I towed it with a one ton Suburban, (don’t remember the year) but it was a towing beast. The trip was about 1500 miles one way and we got about 7 mpg.
We always broke down somewhere. In no particular order: Lost the trailer ball, lost all the turn buckles, lost a wheel on the trailer, crushed the pushpit when the boat got caught under a dock (I’m from a lake who knew about tides?), truck broke down about every 600 miles, outboard blew a head gasket, got eaten by fireants changing a flat, spent 3 hours trying to load the boat on to the trailer as the tide went out. The list goes on.
On the plus side some of the best sailing we have ever had. The whole experience led to us now living in Florida. We finally got smart and began to rent a storage yard and keep the boat in the Keys. Rented Uhaul for s few hours to launch and retrieve.
We would launch using a trailer that had an extendable tongue but even so we never found a good ramp. They were all too short or ended with me dropping the trailer wheels off a ledge at the end of the ramp. This worked fine for launching but was hell to retrieve. We bought a telescoping device that was called a Mast Up that allowed me to raise the mast about ½ way and then jump to the cabin top and muscle it up the rest of the way. We once bribed a forklift operator at a marina the lift the boat on the trailer. They don’t like to lift rounded bottoms.
In short, you can do anything but I wouldn’t recommend it. I was trailering a boat designed to be trailered. Also a beam over 8ft 6 requires a permit and at some point a lead vehicle.