Anypne here have luck with boat transport?

Curious if anyone here has a dedicated boat trailer for hauling larger boats. I've been scouring ebay, truck trader, etc. and see a few dedicated trailers. What about using a low pro or a double drop? I see a lot of boats being transported to / from my region (Lake Michigan).

 

I have made the trip a few times down the Mississippi and, yes, it is very expensive with fuel, time, rations, etc. Took me about 2 weeks to reach the Gulf in a 40' Sea Ray.

I am actually thinking about the market for used boats under 40' and under 17k pounds. Specialized markets can possibly demand more $$$.