Re: Downside of living aboard
For me living aboard was the only option. Graduated college, got a job, bought a 25 Hunter Cherubini, and lived aboard for three years in Michigan. Winters up on stilts.
Later on when my wife agreed to get a boat and live aboard with our three kids it was a different story. But she toughed out the transition with the patience of Job and it's been an adventure ever since. Leaky hatches, passing hurricanes, cramped quarters, etc... Fun times.
A family of five on a 40 footer can become tedious. So we sold it and bought a 50'. Life is now grand. The extra ten feet is like going from a condo to a McMansion. I've lived aboard for about 14 years. The family, coming up on 4.
It is hard to give would-be live aboards advice. Living aboard requires some sacrifices. But you also get many rewards. Most buddies who'd give anything to move on to a sailboat stare longingly into the anchorage while their wives stand firmly behind them tapping feet, arms crossed, and a scowling brow.
IMO the rewards you get are spiritual and/or natural. For a successful live aboard you must be someone who prefers being close to the elements over impressing 'friends' with a huge unpaid house. If a storm excites you then living aboard might be your thing. If you are a shopaholic and compete for material things then maybe not. If you desire hard edge simplicity then it might be fore you. Elaborate landscaping and a maid? Not so much.
I don't think there's any one thing, item, boat, or whatever that can guarantee success. It comes down to personality, type of character, outlook on life, and vision of the future. Why do you want to live aboard? To live the tropical dream? That may not be enough. Moving aboard is like losing weight. Fad diets always fail. You must change your entire lifestyle forever.