We did in fact get a reduced rate by contracting to allow the trucker to wait until he arranged a return load. That took a month which was not a big factor on our schedule, it was early spring in Vermont. I don't recall the insurance details(maybe he wasn't?)

Upon loading(I was not there), I think the bow pulpit was removed.

The boat was very dirty as I recall (it was 20 years ago) from road grime and diesel exhaust upon arrival. But it cleaned up easily enough. Be sure the interior is well sealed. You maybe able to get it shrink wrapped if you're concerned.

That was 20 years ago so the cost then was about 1100.00 That was so much cheaper than doing it by water. It's a great way to extend your time down south. In our case, we were able to spend more time cruising the Bahamas knowing we'd be flying back.