Andrew, why do you want an inboard ? It probably could be done but only with a lot of structural modifications. They also are heavy and quite expensive. It would be easier to get a different boat that was made for one and has one already. You'd need a hull that can support the weight of the engine. Inboards usually are water cooled, so you need a water inlet and an outlet, the latter might also work with the exhaust gasses or you need an extra outlet for this as well. You'd need a way to have the prop shaft without leakage go through the hull to the prop as well, i.e. need to build a "stern gland" into it. You'd loose a lot of space inside of your "classic" with all that. Something that could be done probably a bit easier would be stern drive, but again you'd need to do a lot of structural modifications. Outboards are so much simpler to keep up. If it needs servicing or fixing I can take mine (without the boat) to whoever I choose to do the job. Winterizing is done simply by bringing it home and storing it in the basement.