Interesting thread. I have been all over the map on this. I have a good job with lots of annual leave. Requires lots of hours, but I can work remote
access. So with an Ex and one more college education to help with I will probably work until I drop (I'm 60 now). Social Security
doesn't even come close to what I need to live comfortably.
I get the time thing. My boat projects would for the most part be done if I didn't work a full time job. But as some have admitted, I too probably get more joy from working on the boat and sitting at the marina, than I do from actually cruising around. I do plan to increase my cruising time, but if I don't, it wouldn't really bother me. I've been to almost all the destinations I would sail to. So long term projects are a bigger part of the experience for me.
I have my own reasons for wanting to keep the house (home base). Its not a financial burden, so no reason to sell it. The real burden is all the stuff I own from 40 years of being a good consumer. I am actively getting rid of the junk I have moved from house to house. Feels better with every load I take to the Goodwill (or dump).
Except for financial reasons which has been mentioned many times, I don't know why people have to make this an "all or nothing" proposition. Seems to me the sailing dream for some could be one week out of the year. Don't even need to buy a boat.
Also, I hear people continually mention, "start with a small boat". I too see the merit to this but with some limits. I can't imagine owning an open day sailor without a head
(or cabin). This was fine when I was in my 20's but being 2-3 hours from a bathroom is out of the question now. Sure 95% of the time I would have no trouble making it all day without a potty, but that 5% would truly be embarrassing.