I am 51, and many years ago I had planned the similar dream. I bought a 32' Alden sloop and lived aboard that boat for two years, and while it had decent accommodations, it did start to become claustrophobic to me and I was not comfortable with that and so decided this was not the right boat for me and sold it!
I decided back then, 1998, that if I were going to do this again, I would not consider anything less than a 40' and a double cabin type boat would be a big plus. I did a lot of research for the best suited boat in my financial range and have since July found the boat I wanted and have been sailing and living aboard once again! I am currently in the process of learning this boat and making adjustments and refitting as well as outfitting for extended cruising. I'm planning to shove off in a year or so, buy then, the boat and me, should be well acquainted!