Anyone in hotshot logistics?

find a good mobile welder to fix the trailer. I just had someone come out and replace a utility trailer coupler last week.

Mobile welder would be the most cost effective and easiest solution. Trailer needs to be fixed anyway or replaced, so the $ would be well spent vs. likely spending a few grand to have the boat transported by a big rig, then still needing to fix or replace the trailer.

 

Do this, at night, pack some dynamite. Not only will you get the boat home, you'll create lots of good jobs for construction workers.

 

That’s a nice boat. Since he’s under a time crunch I’d be more inclined to move it now and repair later.
Usually, height restriction is 13’6”, but could be higher depending on the route.
Assuming money is no object, get a crane company to load both boat and trailer on a drop deck trailer. That may give the needed height clearance. A drop deck operator should be versed in wide load permits/restrictions, which you’ll likely need. Or, block up just the boat and put the trailer somewhere else on the trailer.
You may be surprised how economical crane companies are. I used one recently to turn over a floater I was building in my driveway and place it on a trailer. Total bill was a little over $300. You’ll need a crane at the destination, too.

edit to add: the arch on the boat may be able to be removed/lowered to get a lower profile or separate the boat and trailer perhaps permanently?