The tender is a 14ft Twin Vee. For you west coast guys it's basically a 14ft Livingston hull. Except it has a flush deck, console, raised bow deck, 50hp 4stroke.
I would set it down crossways. My hardtop is 11ft wide. I would have the stern of the tender essentially flush with the edge of the hadtop and the lower unit would hang down vertically, then on the otherside the bow would stick out alnost 3ft. It'd look a little kooky, but i don't care. Obviously I would absolutely go overkill with strapping it down tight.
I live on the hook, and my skiff would continue to live in the water 99% of the time. So I'm not concerned if it's a bit of a PITA of an excersize. But it'd be really nice to be able to get it up top for making a long icw run with alot of lift bridges as well as for locks, fuel dock, etc. Same thing for an ocean run, because with the local inlets you really need the right tide and weather to tow thru safely. It's difficult to be able to time that right on both ends. It would also allow me to fish from my trawler. I can't really troll while towing. So as it is i just take my skiff offshore, instead of the big boat.
Lastly, is maintenance. I need to put a new outboard on. By the time I pay a yard for in and out, plus everything else, I could just put that money towards a davit. And that will continue to save me $ every year when I paint the bottom.