I don't know much about investments and a lot of the other things you have asked about, but I do know about some. My background is that I grew up in several different countries, and went to the excellent ex-pat schools in each. They were good enough for me to get into Harvard, and I did not have the guts to say no, although I hated the cold.
I did go off cruising at 42, without a whole lot of assets, and only a 33 foot monohull
, and my girlfriend of the time was having no part of it. I now have a 45 foot Leopard
which my girlfriend (actually, she deserves a better title) and I operate as a crewed charter
yacht in the BVI. I have lived aboard for 23 years and am now 61.
Some thoughts: with regard to kids going sailing, I have yet to meet one that did not benefit from it. Since you abhor home schooling, perhaps you should just take a year off with them and let them profit from the experience. You may be surprised, and you may find a form of home schooling that you like. More likely, you may find a place that you like, and stop for a year or two and put them into schools, there. And the care and quality of THOSE schools may also suprise you, not to mention the incredible experience this will provide.....not to mention something for future college admissions officers to underline as interesting and unusual. Medical
care is not the only thing that exists in other countries, often of higher quality and lower cost than ours! How do you think all those third-worlders get into our top schools?
Give it some thought. If the idea, or the experiment
, sound good, then go now and learn to live a bit less expensively. He who owns little, it little owned. Very true. A simple boat, even a big one, can be much more fun than a complex, super comfotable one. And you can learn as you go. I grew up with absolutely NO mechanical experience and motion sickness. I did not know the difference between a flat head
and a phillips screw driver, and forget about Allen keys! Really. But, I can now fix most things, install almost all of them, understand almost all of them, and can do it underway in rough conditions. And, I have found the process very satisfying. Not necessarily easy, but satisfying.
I always recommend bareboaters to charter
the simplest boat they can, and not fall for the marketing
hype of features that the big companies provide. That way, they sail more and enjoy where they are more, although they may not learn as much about where the repair men
are. And, they may never have to meet the Charter Companies service
boats! Same thing goes for cruising boats.
If you decide against my experiment
, and you probably will, then before you plunk down your hard earned cash with the Moorings, realize that a company that guarantees you that they pay for the maintenance
has a vested interest in cutting corners. Sorry, but that is the way it is. You would think that if they wanted to sell you another boat in the future, they would treat you like a treasured asset. They will, when you visit, and they will do all sorts of things to get your boat ready for when you visit (including cannibalizing your sisterships), but when you are gone, the shoe will be on the other foot.
As the buyer of a former Moorings Crewed Yacht, I could give you all sorts of details....just beware. And the salesmens' mantra that "after phaseout, all boats will be in excellent condition and equal" is just not true. You CAN get a very good boat out of their fleet, but it is hard work and takes time. Check my previous posts on this. You will earn everything you get, when the discussion hinges on whether something is "damage", or fair wear and tear.
But, I do have an alternate suggestion. Buy an already operating and successful privately owned crewed charter yacht. You will save by buying
used. It will be in excellent condition and very well equipped. You will be able to add whatever you want. It will come with crew competent in its operation and upkeep. If you don't like the crew, you will be able to get a crew you DO like. If you want them aboard with you, that will happen. If you want them off when you are there, that can also be arranged. You will be to use the boat whenever you wish, wherever you choose to move it, and as often as you wish. The rest of the time it will be earning its keep and being kept in top shape. Don't plan on making any money at this....but you will lose a lot less and have a lot better boat than any of the other options you are looking at. There are a few brokerages that specialize in this.
You may want to keep the boat in the Caribbean
in the winter and spring, and then move it up to the East Coast/New England
for the summer. That puts it in the right places at the right times for both you and for chartering, although I personally don't mind the Caribbean
in the summer......lighter winds, more anchorages
available, much less crowded and hurricanes are a manageable risk. But then, like you, I enjoy the heat and humidity.
You may find this lifestyle so appealing that you do it permanently. Or, you may choose to take the boat to the Med for a year, or some such thing. Or, in time, you (and heck, maybe even the kids) may choose to take the boat out of charter and go cruising. All these options would be your decision, and none of them would be bad.
Then, you could live somewhere you like...you have many suggestions, and personally, I would live somewhere I could have the Catalina
nearby, but that may be really expensive. You can keep your company going without getting stale, since you will be spending lots of time on your boat. And, you can evolve your lifestyle as your time and finances evolve. You won't be risking much, and you will be gaining a lot....and a lot more than if you put a new boat into the bareboat
business. At at the end of the five year period, your used bareboat
will not be worth any more than your more used crewed charter yacht, and the later will be better equipped and in better shape. You will have gained the charter income to offset the difference, it is absolutely true, but I am betting you will prefer my option.
But whatever you do, do it soon, enjoy what you do, and don't look back at the other options you decided against.