Nice to see the OP is back, and many happy returns.
I am still not clear about the weight of the boat which seems to be an important issue. But even if it was heavier than the OP thought or claimed or whatever the trucker is still the one who is required to know for certain that his truck and trailer can carry the weight. It really does not matter what the lift operator says about the boat weight.
There are scales at every Flying J I have ever seen, not to mention almost every other real truck stop anywhere in the US. Truckers use them all the time so they know before hand what will happen when they hit a DOT weigh station. I have seen threads, especially at SA and the Fboat yahoo groups, about guys hauling their boats stopping at a truck stop to get a good idea of what their boat weighs.
Not to mention truckers hauling a wide load have to keep a log which includes what the boat weighed at the DOT weigh station. It is not rocket science to find out what a boat weighs and citing a lift operator seems to be one of the worst ways to do it.
As to the condition of the boat that is really a non issue. Most of us have seen trucks on interstate that are carrying crushed or junk cars. The fact that the load is not ship shape and in Bristol fashion does not lessen the responsibility of the trucker to know what weight issues are and to conform to trucking rules.
My view is the legal
analysis is fairly simple. Two parties entered into a contract and it was not fulfilled. While courts often will go easy if there is a good faith effort to fulfill the contract that does not seem to be the case here.
A jury is charged with resolving issues of fact. If the facts the OP posted can be proved in court (the trucker was providing false information about the progress of getting the load to its destination) and the OP suffered loss because of this the trucker may well be liable for those losses (stuff like travel and lodging resulting from delay in the boat being delivered).
In any case the trucker will have a hard time explaining why the boat is more than a month late being delivered.