I think if you are willing to pay the price for the necessary hitch extension and related parts, you will have no issues. You may need a weight distribution hitch and extension. Like most things, there will be compromises. For example, the longer the extension, the less weight your trailer can carry, and the less your boat can weigh. If you look at the rigs of other TC'ers, you will get a pretty good idea as to what you can do. If you choose to split hairs with decal weights, you will probably have to make more compromises.
I only flat tow my Samurai with my present setup, but have towed several different trailers with other trucks/TCs in times past.
Wayne