I lived on a boat on Shelter Island (pt loma) from 2008-2010 and I wish it could have been much longer. I moved off because I got married and two people on my small sailboat is one too many (but many people do that too). I can honestly say that it was the best living experience of my life. I think it takes a certain breed of person to enjoy it though. You are living in an small RV, and not some sweet 5th wheeler kind. But marinas have great shower, laundry, and workout facilities. Many people live on boats for many years including happily married couples.
It was a great sailboat to live on a reasonably problem free. There is nothing like eating your breakfast in the morning sitting on the back of your boat looking out over pt loma with a coffee in your hand. Or looking at the hill of lights with a good beer. Falling asleep listening to the wind in the rigging and rocking ever so slightly. The quarters are cramped, but you have the whole bay to explore in your dingy, or if you want to live in Coronado for the weekend, just drop anchor at Glorietta bay and pretend you are on vacation (my wife and I loved that the most). If you have a long weekend head up to catalina and get away from the craziness in Avalon.
The cost breakdown was quite affordable. I purchased a $38k Catalina 34 from 1985. The Slip fees were $500 a month, another $150 for the liveaboard allowance, and 30 bucks a month for bottom cleanings. If you do the maintenance yourself, expect to pay 1-3k a year in repairs for a sailboat of my vintage and quality, cheaper if you do most things yourself but lots more if you farm it all out to contractors. Needless to say, that is the cheapest one can live anywhere near the ocean, let alone an inch away. Make no mistake if something serious is wrong, or you buy a total lemon, you could blow a lot of money. Not unlike a leaky roof or a broken furnace. But being handy and cheap helps keep the costs to a reasonable amount.
I transferred ownership of the boat to my parents because they wanted a winter escape in sunny SD. The boat market for this model is still what I paid for it, and I think we could get a bit more because of the work that we have put in. And with a sailboat gas is cheap. I think I put about 30 gal in a year, and we went out at least once a week, plus another ~30 gallons to go to Catalina and back.
I will be moving back to a boat one day, perhaps not until I am much older and a family is through the pipes, but it will happen.
I have lots of other thoughts to share on the pros and cons, so hit me up if you are seriously interested. Your inquiry is probably not serious, but I loved the experience so much I felt compelled to share.
