Re: Thinking about doing a repower. 3.7 to small block Ford
Well, the 3.7L was an inline-engine, so you'd need a new set of motor mounts for the front, the transom plate wouldn't likely fit, either. I don't recall that the 289 was ever used in a marine application, at least not by Mercruiser, so finding a coupler might be difficult as well as exhaust manifolds and exhaust y-pipe. The gearing would be the least of the problems you'd encounter.
As much as I like my Fords, it's not really an easy swap unless you want to source a lot of NLA parts and do custom fabbing of your own. Either refresh the 3.7L, or find a junk boat with a good engine and swap all of the parts off of it.