I bought my first boat in 96, became a legal livaboard, did a lot of work to her and dreamed of taking off one day and being self sufficient. Sold the boat in 04 and went back to Europe to be with my father for his last few months of life. Came back to the States later that year, bought another boat and have spent the past 2 1/2 years working on her. I no longer have realistic dreams of the South Pacific, but want the boat capable anyway. I became a legal livaboard recently when the opportunity came along, before that I was a sneakaboard. I'm no prude but my dock did have a few "low lifes" living there, drink, drug type thing, most have been evicted now. Only worries I ever have about those types is possible theft. There are about 5 livaboards on my dock, a retired couple in a houseboat, a retired IBM female, a guy who just got his license to sell boats, and another guy who lives on a junker, but he's always been cool.
The livaboard life suits me to a tee, I feel independent, it's quiet and while I can talk to anyone in the area, no one invades anothers' space obtrusively.
I can't think of a way of life that affords more freedom than this, and thank goodness it's not a viable choice for most. I'm in my late 50's, and look forward to the last 20 years of my life being spent my way, free of as much hassle as possible. Boring for most I'm sure, but that's ok by me.
I think your question was a good one, and I'm happy but a bit surprised that my life ended up where it did. Everybody will have their own road, but it's nice that we can meet here and share, if we want.
All the best.