What a great question, and one that I've been asking myself lately. I lived aboard for a few years 20 years ago and absolutely LOVED it. My Catalina 36 was a palace for one and not bad when my future ex-wife and dog came aboard. We moved off and started a family on land. It just seemed easier since we were marina bound, not cruising. Twenty years go by, my son's off at college, ex-wife is long gone and I sit here sometimes wondering if I really need all this cr@p I seem to have collected. For me, it comes down to things like where would I put my 2 cars & 2 motorcycles, how much I'd miss my workshop, where would I put my 6 guitars (moisture is bad for them), my guns, my books, my kid's room when he graces me with a visit, and on & on. Fact is, I'm just used to comfort now. I'm 58, not 35 and comfort is a good thing. I like my 70" TV and my big comfy bed. Fortunately, I don't have financial issues as my house and boat are paid for. So, I keep the house and visit the boat several times a week. I never had the dream of sailing away, there are too many other things that I enjoy doing. So, although I do think about it from time to time, I imagine I'll end up keeping both.