I don't think I'd ever want to live on a boat. If I'm tied to a dock most of the time, I may as well live in something with a decent bathroom. I like the idea of sailboats, and enjoy sailing (small stuff: Lasers, Sunfish, etc.), but they aren't incredibly practical. It's annoying enough to rig a small boat, thank you very much. Sailboats also have additional risks of tipping over, ropes catching you, booms hitting you, etc. I've also had the misfortune to be sailing a boat when the mast snapped in two (it was carbon fiber mast and I was hauling ass in huge wind and decent swells). There's not much scarier than that.
Of course, the upsides to sailing are also pretty big, IMO. You can save a lot of fuel if you don't spend all your travel time on narrow, windless, inland waterways with currents, etc. They are also pretty much silent under sail power, except for the sound of the boat slicing through water. It's also a great feeling to harness the wind for propulsion. They're less automated, similar to the difference between a manual and automatic transmission in a car. I love manuals. There are also a ton of sailboat races for all types of boats, if that's your thing.