That is a tough question. Most people think that it's too expensive to have a boat transported now. There are probably only a handful of people on OSO (I am one of the handful ) that know what it's like to haul boats for a living, day in and out. It's not as easy as people think. The customer just knows his boat went from point A to point B.
I would think that the more expensive boats would be trailered on the landoll. Too be honest with you, I don't think .25 per mile would benefit you. Figure now you have to buy a larger truck and the trailer. Then, the semi truck you buy gets no where near the fuel economy of your 1 ton truck.