The most interesting, imho, thing, is that the majority seem to focus upon making their new old boat pretty, as opposed to functional. Or at least, non-sinkable, non-leaky...
Imho, the failures are those with arguably, unrealistic expectations. Mostly in the financial area, it seems. But also in their perception of what the dream is.
THIS and THIS!
Really excellent observations. I have only been living aboard for a few months, but the one best piece of advise that was given to me was to keep realistic expectations..of yourself, your needs, and the boat. I live simply, but I live well. My boat is my home, but it is a boat first and foremost. Basic maintenance and safely come before beautification.
Unfortunately, I see many in my marina that see their "boat" as purely a cheep means of living. They don't sail, they know nothing about their boats, and know absolutely nothing about basic maintenance. A few weekends ago, once such boat took on over a foot of water while the owners were away. Many of us rushed over to bail the boat out. When they returned, I started asking them basic questions regarding through hulls and other possible areas of ingress. They just looked at me like I was speaking Greek. There is no excuse to not have a basic understanding of your boat, especially when it is your home.
Speaking to the financial bit, many people are lured into the dream of living aboard thinking that it will be cheap. Boats are a constant project, especially for us with 30+ year old boats. I love working on mine, but I find sensible ways of doing it. Down in Annapolis there is a fantastic store that sells used items. Without them, I wouldn't be able to afford to work on my boat.
I don't want this thread to scare away any potential liveaboards, it can be a really wonderful and rewarding lifestyle. But it is important for people to do their research and understand the ups and downs. And above all, be realistic!