When I was looking for a 440 I investigated transporting from Seattle to Lake Michigan via truck, as the upper tier of the country has far fewer highway impediments than the mid and southern routes. Seattle to Menominee, Michigan was my plan as an excellent boat transport company is located in Menominee. We ended up buying our boat in Austin Texas (Lake Travis) and trucking it north to Green Bay. But even that route has become troublesome. Of course any boat on the Great Loop circuit could be moved to the Gulf Coast on its own bottom. We did not remove the flybridge, but did employ a lead pole truck for most of the route. The height on the trailer was 15' 4" with the venturi, arch, sunroof, compass, seats removed (see photo).
By the way, back in the day the now defunct dealership in Sturgeon Bay, Wisconsin sold a fair number of boats on the Great Lakes. Unfortunately, most of those fresh water gems have been snapped up by Loopers.
Here's a link that you've probably already seen. The OA trawler/motoryacht offerings in your desired size range have pretty much dried up over the past year. https://www.boattrader.com/boats/mak...xander/page-2/