Gas Vs. Deisel (are we crazy?)
Agreed that an inboard diesel is preferable, but your trip is possible with an outboard. Check this link for a fellow who traveled from NY to the Keys and the Bahamas on his O''Day 25 with an outboard. He had his troubles, but he made it. In fact, I just went sailing with him one afternoon in Key West earlier this month. I think the bottom line is how well YOU are up to dealing with an outboard for such a voyage. It''s doable, but not without some risks over and above using an inboard engine, whether it be gas or diesel.