On my 30th birthday I bought my very first sailboat and I had virtually zero sailing experience.  My first post-college job took me offshore on large oil and gas vessels so I had an idea that I enjoyed the remoteness and that I could take the conditions. I wanted a place to stay locally in the bay area so I had a good excuse to get a boat.  There are pros and cons to living aboard a sailboat but it's hard to argue against a waterfront view in SF bay for $600 a month... especially considering SF just made it to the top of the list for rental costs.