Ryan,
I've towed a bunch of bigger boats, 28s, 30s, 35s, the biggest issue is the ramp transition. Steep ramps have a very pronounced transition from the flat of the parking lot onto the ramp itself. Too steep a transition, and too long a trailer tongue, and the trailer will ground on the break point before the back end of the truck can get back far enough to pick the coupler back up again...if you know what I mean.
Our triple-axle Myco had a VERY longue, and on a low mounted hitch, she wanted to drag...