Yes, definitely, do it. You'll have a great time.
Being able to
work remotely makes your financial situation wonderfully elastic and resilient. I think that's great. Aren't we computer nerds so fortunate in this era?
My only comment is that 'friends visiting' may be a lot rarer than you expect (and they say). Since it's so far away, especially from
California, and people with jobs usually only blow a week a year on something like this. And, weirdly, everyone who visited us so far has insisted on spending at least a few days in a
hotel. Which means, out of a week, they've sailed with us for only a few days.
This is a very personal decision, but we have a larger nest egg and a less expensive boat. We would have an even less expensive boat if we didn't have
kids and planned to stay in the Caribbean. So, if I knew you and we were talking in person, I'd hint that you should look at lesser boats and see if you could still have a happy and comfortable lifestyle on it. Maybe look at the boat as a tool to enable experiences, and nothing more. Because there is a joy in having the boat be a little more 'flippant' -- not a large fraction of your net worth. Because sometimes your idea of what the most fun thing to be doing changes, and at that point, there is a freedom in not feeling so financially tied to the boat. What if in two years you decide you want to rent a house in Kyoto or Paris for a year, or travel by land in
South America for two years-- isn't it nice to be able to just stash the boat in the mangroves or at
anchor without worrying too much about it? Or you get to
Malaysia and balk at crossing the
Indian Ocean and rounding the Cape of Good Hope -- what a luxury to think "Screw it, I'll sell the boat here, as is where is, for half what I could get in America and backpack around
Asia for six months"? Of course, everyone is different, so I am self conscious about saying this online.
Oh, and on a monthly budget -- my
family of four averaged about $2k/month. That was completely comfortable. We are not extravagant people, but we aren't frugal, either. I feel like we did whatever sounded fun that day, without much regard for the cost. We sometimes stayed in
marinas, rented cars (sometimes for months), and ate out often. That we like rural places, and spent weeks and months snorkeling off deserted beaches, dramatically lowered our average and balanced the time we spent in expensive islands.
This excludes all boat upgrades, because, to be honest, I am embarrassed by them and don't even want to try and add them up. I initiated a lot of completely frivolous and expensive projects.