I had always dreamed of owning a boat and living aboard, several times over the last 30yrs my wife thought of just owning a sailboat, but her thoughts would soon fade
About 4 yrs ago she got really sick and was taken to a hospital while I was out at a race, so I didn't know until I got home, once I found out I quit racing after 40 yrs. One day I took her for a drive to get her some fresh air and we drove by a lake were she saw a couple sailboats, she soon started thinking of owning one again, I told her if she was serious, I would sell all the race bikes and get her a daysailer, well she was serious, we looked around, found a fixer upper, I sold all but one bike, bought the boat and sunk all the bike funds into it.
What started out as a weekend sailing, fixing and get away thing soon became a extended weekend get away..........(for her, I had to work), then it turned into only coming home to wash clothes then head back to the boat, we now live aboard full time and it was I that was dragging anchore not wanting to sell the house.
Bottom line is don't rush it, make every trip out enjoyable and comfortable, My wife loves every second of living aboard, her health is better than ever and she'll never be on land again ( her words, not mine )
A funny little side ditty, our first boat was a 26' daysailer and she banged her head 10 times a day in that thing, when we got our 37 footer, the first thing she did was fall down the campanion way, twisting her knee, she was useless for 3 months
1978 Tayana 37
1955 Blanchard 51 Custom ( I got a woody )