It sounds to me like the "trucker" really isn't a trucker. Sounds like Bubba with a 1-ton pickup and a trailer.
Granted, an aforementioned Bubba could have a DOT number, lots of them do. You see them hauling a goose-neck 5th
wheel trailer with a couple of cars on them, or a flatbed with freight on them. We call these guys "hotshots", because they often go into the
oil fields hauling smaller loads of drill pipe and machinery
parts. They have to have a DOT number, insurance (both cargo and unladen) and the proper licensing. This sounds like the type of truck he contracted.
I would never allow a hotshot rig to haul my probably overwidth home afloat. I would want a bona-fide
marine carrier such as Dudley or Joule. If he has contacted a boat transport
broker, and went with the cheapest, no telling who he actually got.
As a flatbed trucker, indeed, according to the regs in 39CFR, an open
deck is supposed to stop within the first 50 miles to do a cargo check (because the freight often will 'settle, and required adjusting the tie-downs)and every 150 miles or 3 hours afterward. Most of us stop more frequently, some don't. It depends on the load. A solid block of something probably won't budge, a load of loose iron will walk around and drive you nuts.
The overweight issue is actually
equipment related. On a class 8 truck, most states allow 20,000lbs per axle, 12,000 for the steer axle (because it only has
single tires and depending on the tire rating), 34,000 lbs on a set of tandem axles with dual tires. A 'spread-axle' like mine can handle 40K on the spread, but no more than 20K on each axle (this on a trailer). So, if the equipment in question is a hotshot, he may well have exceeded his axle rating, an which case he should have known this.
The OP as the customer is not responsible for the truck
repairs, or the repositioning of the boat. The repositioning should have been done the same day, at the same facility that loaded it.
Repairs to a damaged trailer only are paid for by another party if they damage it, such as a guy stabs the forks of a forklift through the wall of a trailer, or drops the cargo through the floor, then the loader/unloader pays for repairs. Not the customer that owns the freight, unless they are the ones loading it. Damage from shifting freight is on the trucker.
They've hijacked his boat.
The OP is being el-screwo-ed.