Some other generic advice on large boat trailering from previous experience:
The KEY dimension is usually not the width or the length, but the height from keel to top of hull. Anything over 12 feet becomes very problematic because of bridge clearance.
Be sure that the trucker agrees HE is responsible for ALL damage on arrival. Don't leave room for him to try to wiggle out and blame the boat yard that did the prep. Once he signs for it and takes possession, it's his. It can be a good idea to find a trucker who has worked with the prepping boatyard in the past had has a good working relationship with them. Inspect the truck BEFORE loading. If there are missing or damaged fenders and//or mudflats, do not put your boat on that truck, road gravel can really do a number on your hull in 2000 miles..
The assembling boatyard can really be your best friend. If they are good, with highly experienced staff, they will notice damage that might otherwise be missed. Be sure you are there with a camera for unloading. In my experience, the mast and rigging is the most likely to suffer damage. If there are any parts that haven't been unwrapped and inspected when the trucker is ready to leave, make sure those parts are NOT signed off as "accepted in good condition".
Make sure you understand the trucker's insurance, their deductible, and policy for handling small claims. If they have a $5000 deductible, how will they handle a $6000 claim? They will probably not want to file an insurance claim to recover $1000, but they still need to pay YOU.
Be sure that the quote up front includes ALL the expenses. Over-size load permits, chase cars, trucker overtime, fuel surcharges, etc, etc. The incidentals can make a very long list that can add up to a bit peice of the final bill. The rules vary from state to state, and some of them conflict in almost funny ways. In one state the oversized load could only move on the roads during daylight. In the NEXT state, only at night. Really?
Make sure the boat is sealed as close to air tight as you can get. You do NOT want diesel soot from the truck getting inside! You'll have enough fun cleaning soot and road grime off the outside.
Give the trucker a camera. Pictures of your boat in the high desert, and mountain passes will be fun to have.
I had one trucking company come in with a low, but reasonable, bid. They came highly recommended. In the weeks before the trip, they started to add extra fees, one after another, after another, until they were the HIGHEST bid. What happened? They had bid assuming they had a return load. They lost that job, and with out a return paying trip, they no longer wanted the job, but didn't want to say so. They just kept upping the cost until I told them to get lost.
And one last thing... on a cross continent trip, remember the weather in the mountain passes! Outside of high summer, you might need to prep the boat for freezing temperatures!
Nanny Cay, Tortola, BVI