Not an avid seaman, but smart and good at doing just about anything he sets his mind to, from my observation. A driving factor is that they aren't going to be able to maintain their current large home and grounds. So what to do... That's what has him thinking of alternative options. My suggestion to him is an RV, but his thinking is if SHTF, an RV is going to get you stuck somewhere you might not want to be, as roads may be impassable.
So, he has a lot he is considering. I have an RV so I'm perhaps biased IMO. I've seen some mighty good ideas, mentions of things to consider on the thread and it's going to be helpful to them, I'm sure. Everyone's situation is different of course, and we each have our dreams and aspirations in life.
One thing for certain, have a backup plan if things don't go as planned.
The boat was pretty stinky too - and always noisy at night. Some kind of weird pump always running or something. They had a lovely kitchen with granite so it was not a low end boat - but for day in and day out living it had a lot of drawbacks.
Having a house as a base and an RV seems like a pretty great way to go. You can go a lot more places in an RV - in a boat you are pretty stuck as so few places are easy and safe to get to. They were in CA which has suprisingly few destinations sea wise - they went to Catalina a lot.
Neither RV nor sailboat, cruiser is an answer for someone seriously concerned about if/when SHTF. If that is the major concern coupled with quiet and solitude and not travel, then would suggest the specific sites that sell SHTF locations— like in Idaho or mtns. Some of them out West are ornate self sufficient caves/ natural mold design into the side of a mtn sort of thing. Independent water source, solar power/batteries etc. All the technology of RV and sail (to include the wind generators) have been applied to the SHTF scenario.
But, have to say— if medical/clinical needs are in the picture— one has to be within reach of professional medical help if chronic illness, etc. Will say that along with the SHTF back up location, one can venture out within travel range of the location in a Class B RV or tow a high tech small trailer (so one has wheels or if needed to jettison and high tail it to SHTF location).
all the above from the perspective of “what could go wrong” coupled with a more apocalyptic SHTF mentality (which changes a lot— like— food in storage for 10 years in situ, with plenty of water, heat source etc— and discrete).
We definitely wouldn’t trade our 15+ years of cruising and living aboard experiences for anything - it was very enjoyable even with the problems which are inevitable. We saw many beautiful places, met some fine people, made lifelong friends and have many fond memories. When people tell us they have always dreamed of living on a boat, I say, try it...what’s the worst thing that can happen? If you decide you hate it, then you can always sell and try something else. But at least you did it.
Your friend can always buy a smaller house on the water somewhere and keep a boat docked behind it for trips. Ft. Lauderdale is a wonderful place to do that as is the Gulf Coast of Florida like Venice, Longboat Key, Sarasota, St. Petersburg, etc. Another idea is buying a house in the Bahamas. HGTV has a program called “Living the Bahamas Life” and there is a big variety of homes at all different prices throughout that island chain. Many airlines fly there now, for example, Marsh Harbour, Freeport or Nassau so family can come visit. There are plenty of options for your friends.