The OP raises so many issues here. The main one I suppose is that everyone has a completely different set of circumstances, values, goals and how they chose to live their lives.
Most people follow most of the well worn paths in life... get an education, work which pays well enough to live well and save for a a future... which often means/includes passing assets / inheritance on to your offspring or partner, and money to pay for your lifestyle when you stop working for whatever reason. So most people maintain "investments" for this purpose.
A common element on SN is members incorporate sailing as a large component on their lives. And there are many ways to sail... day sailing, racing, weekend cruising, long term and distance cruising, part time use or full time live aboard and all manner of permutations. Some are professionals... run charters or are mechanics and so on. So clearly there is no right answer or path here... each one will be what works for each sailor and their circumstance. There will be common paths but likely no identical ones.
I began sailing in mid life. I was essentially single as I had divorced and had no children. I was self employed and had made come money which sat in a bank. I was not thinking about heirs or even retirement at the time. My father had recently died after working his whole life without a retirement. Why wait until you're too old to do the things you want to do?
My "discovery" of sailing was complexly accidental. I had no exposure until very shortly before I bought Shiva which is the only boat I have ever owned and still do since August 1985. Since I was completely new... sailing seemed to me, at the time, like I was opening a door into a previously unseen and unknown universe/ It felt similar to how I felt as a college freshman entering architecture school to learn a profession I had chosen to do for my "work" in life. Like architecture... sailing would have to be "mastered". I loved the idea of taking in a new "discipline" and so "late" in life. I knew there was a lot to learn. So I began my studies which included books, and courses and of course real time experience with the boat I bought.
Clearly buying a "serious" boat without a knowledge base was risky. I had no experience to inform my decision... just books and advice from a trusted friend who sailed... and my own gut response to what I saw in the boat.
The decision included the idea of getting a boat I could:
aail single hand and therefore short hand
do well in ocean passages
comfortable to live aboard
afford to purchase, outfit and maintain
I spent Spring 85 and part of Summer looking until I found the 36s. I was in full learning mode. When I closed I was faced with hands on experience learning how to sail.... and what to do for upgrades.... I had to learn to care for a diesel... I was not someone who messed with cars or motorcycles. No interest in such things.
As the first years ticked off I was in a full immersion mode. I spent all my waking hours in learning mode aside from doing my work. And I realized how this boat was a perfect match for me. I suppose it's sort of like falling in love and getting hitched.
I realized that my social life would be radically different living on a boat and even more so in new and unfamiliar places. I wanted a partner to share the experience and be into it as much as I was. I knew this was a long shot... but I kept one eye open. When the decision was made for my "sabbatical" I left single and unattached. Pretty hard to hook up with a woman of the "right age" who was unencumbered and not into her career to take off and live on a sailboat. I did meet several interesting ladies along the way... but no "keepers" as expected.
My "sailing sabbatical" did not disappoint. I had all sorts of experiences I never would have had as an architect in NYC with a sailboat in LI. I met remarkable people and have great memories. I became a very competent sailor of MY boat. And I did some deliveries of other boats. Not something I enjoy as much as my own... but I made some money and chalked up experience.
I decided to "return" to civilization to pursue a business idea which came to me sitting in the cockpit of my then girlfriend's boat in the Canary Islands. It was a boat related idea and something that I needed to try to make happen but not in the Canary Islands.
I returned to NYC and lived aboard in LIS Sound, got a car and worked on the project development/business plan for about a year. I cruised locally and at one point almost sold the boat when it was on the hard in winter storage and I was living in a small apartment with my new GF who became my wife. Business plan did not get funded... and we decided to not sell and use the boat and have been doing so since the late 90s. Wifey is not a sailor and doesn't want to be. But she does love the boat, being on it and visiting places. It's our summer home, and our vacation.
I am so used to having this as part of my life... selling the boat would be like selling my left arm. I have had this boat half my life.... more than any other material thing I own... this boat as been with me.
I can sell the boat and get tens of thousands of dollars. I can't take them to the grave... wifey will get them if she outlives me as she likely will. Or she can sell the boat on my passing. As long as we can use and enjoy the boat we keep it as it's our home. And we do love being there.... and there is where ever the anchor sets.
I would the next owner/caretaker to be someone who appreciates and loves her as I have... though that is impossible. To next owner she will be just a well found and well cared for good sailing old sailboat. But who knows... maybe the next owner will fall in love as I did.
You don't sell what you love and what has "cared for" you for decades through calm seas and gales.
Love song for Shiva: