Planning a liveaboard boat in the future

Your idea of a house and a smaller boat is really good. About the "significant other", you've been married. You know that what most women want is stability / security. A guy living on a boat is a fun date for a bar fly, but good luck finding a significant other that finds it attractive. Even if they pretend, you can count on the boat getting sold will be priority #1. Now a guy who owns a house AND has some toys like a boat is a catch. You've mentioned 'at comparable cost' a couple of times. They're not. Boats are big holes in the water that suck money out of your wallet by the thousands. Very little loses its value as fast as a boat or costs as much to maintain. You mentioned cruising up the coast....and burning 30 or 40 gph at 20 kts. A 100 mi trip takes 5 hours+ and 200+ gals of fuel. That's 1.5 hours and maybe 5 gals. of gas by car or 2 hours and 10 gals. by motorhome. One other thing about that significant other. You think apartments have thin walls? Try living on a boat with your neighbor 4' away for a lack of privacy. I've worked on boats most of my adult life and the one thing I've learned is that the best boat is the one your friend owns. You show up with the beer and leave the hassles and expense to him. There really is only one good excuse for living aboard a boat, and that's an addiction to boats and salt air. It does get in the blood for some guys (but much fewer women).

Or an Albin Weekender, like this one:
www.odincharters.com

28’, single diesel, plenty deck space to lounge and fish during the day,
2 beds, a small galley and a head for living on the hook a few days now and then. They go from $45k to about $75k
Albin 28TE if you want to search.

I would say for the time being buy yourself a house/condo. Join one of the boating clubs for a year. The fees are cheaper than owning your own boat, don't have to worry about any of the ownership hassles such as dockage, repairs, keeping it clean and you just call, use the boat and pay for the gas you use, pull back in and hand them the keys.

I wonder if there is an opportunity to rent a bare charter and stay at the dock for a month or 2 to get a taste of what it means to 'live aboard". If you're new to boating you may not really understand what that phrase entails?

Did exactly that years ago in St. Croix: Young Wifey and I was on vacation and stayed on a sailboat at a dock in Christiansted for a week in 1984.
Couldn’t take the boat out, stuck at the dock, but great experience. ($25 a day or something back then, Airbnb way before Airbnb was invented)
We ended up buying a boat a few months later right there and lived on it for 3 years and sailing the Virgin Islands on days off.
All good, loved it.

There are certainly people who enjoy living on a 35-foot yacht all year round. It just wouldn't be my thing. I drive a small luxury engine, 40 footer. For the summer I think that's okay, but if you can only be inside in the winter, I'd rather be inside a house somewhere. To me this is way more comfortable, although my boat is designed for year-round use as well. It’s just not my thing to spend all year long on the boat…

If I were you, I would make sure that double glass panes are installed. If possible, no simple air heating, but a heating system that runs on hot water or oil heater… A good insulation of the hull and the superstructure…

I think you should bear in mind several options. Personally, I need my place sometimes…which I don't always have on a boat.

RER, ok, when the OP is in Southern California, you're right, none of that is needed. But I think it wouldn't be a bad idea to be prepared for an "emergency." And maybe you would like to go somewhere else sometime, where it can get a lot colder at night during winter. Well my credo is always: BE PREPARED FOR EVERYTHING! :-D

JeffinSoCal, if you can share your membership and split it with your friend, that would be very nice. You just have to consider a few things in beforehand, and if you do, you can save a lot of money. If you just rent boats for a half day once every five to six weeks, it would be less than joining the club. You just have to think about what you prefer. In the club you would also get a bunch of free instructions…depending on what you prefer and how often you want to use a boat, you can decide what option fits best to you!

Personally I would not join a club if I didn't have a boat. Solving specific boat issues among boat owners is generally my experience at clubs, as well as discussing the latest cruise, if it's a cruising club, or fishing techniques if its a fishing club. A yacht club is more of a social experience than a learning experience. I think I'd rent that boat at the dock on a per diem basis to truly test my desire. If its an active dock you'll get as much info there as you would from a club, maybe more. Also you'll get an opportunity to learn about a range of boat models if the facility has any size and has a good transient business.

Check out Freedom boat club. I have a few friends who use it. You get to use one of several center consoles, lowest cost/commitment way to get into boating with a newer reliable small boat. They do all the maintenance and offer lessons. Might be a way to gain experience while on the waitlist.