I think people overlook a very important point. To make this work you are committing all your vacations for the next 5 years (or more) to this boat. Said another way, you are pre-paying for your vacations for the next 5 years whether you go on them or not. My $0.02 - You have to be really solid with this concept to go any further.

You should consider your health in this decision, and the health of your significant other, or whoever else you are counting on to join your adventures.

If you or spouse hurts their back shoveling snow and you can't sail for an entire year (or ever again), how's that gonna work out for you?

We have been happy chartering 10-14 days a year for the last 32 years. We love it. We have skipped lean years when kids were in college. Now we could even see going to 30 days a year. That's what I consider as roughly the break even point for the rent/buy decision.

So the trade-off for us at 30 charter days a year is balancing flexibility of lifestyle, risk of not being able to use the boat (i.e. paying for a vacation I can't take), and the opportunity cost of tying up the money. Remember that as part of this equation you need to add travel costs getting to your boat: hotels, rental cars, flights, taxis, airport parking fees, etc.

Your risk aversion factors in. I'm personally risk-adverse, and having a nest-egg in the bank to cover an unforseen crisis helps me sleep better at night. Others may not have this issue, or have more 'disposable' capital so their risk is covered.

Finally... there's an intangible that is hard (impossible?) to quantify. Owning a boat in the Caribbean may well mean a lot to you. It can generate a sense of pride. A sense of commitment and belonging to a place you love. That may be worth factoring into the equation somehow. It's a person choice and only you can answer that question.

So far we've been very happy to charter every year, and keep our money in the bank where it has grown and helps pay for our next charter. Perhaps when I finally retire this balance will change.