Re: Downside of living aboard
The way to avoid failure is to sample it. Don't get married after one date.
The longest period we spent on any boat we owned was 13 weeks, and at that time it was a 52ft and nicely fitted with everything you can think of. About week 11, I was ready to get off, enjoy the amenities of living ashore (endless showers, no anchor watch for my house, no weather planning, no ferrying supplies by dingy, etc, etc) and dare I say enjoy going to work (not that you cannot work and live aboard too).
We love to sail. We cruise many weeks each year. We day sail whenever we can. We go south and charter in the winter for a week or 2. Every time I get on the boat, I'm happy and excited to sail and cruise.
We're not cut out to be live full time on board. The older I get, the more creature comforts matter.
I have friends that have lived aboard for 10 years, sailed west coast to Australia, now heading Panama to Europe. Older than us, but they love it. To each their own.
Our advice, at least go out for a long cruise (months) before you commit to the lifestyle. It's not what you think it is, and it maybe great for you, maybe not.