My wife and I lived on a 33" Hunter 336 in Berkeley, California for 2+ years. Our first child was born during that time and lived on the boat until he was 18 months old.
It was a great experience; I'm very happy we did it.
Our boat had some nice amenities which made it a great liveaboard boat: two berths (so our son had his own room), bathroom w/ builtin shower & electric macerating freshwater toilet (which I installed), stove, oven, microwave, electric hot water, fridge, large kitchen sink. We typically would shower on land at the Berkeley Yacht Club which was very close to our slip (the bathroom on the boat doubled as the shower and it was inconvenient to get the bathroom floor wet). A dedicated shower is the only major feature I'd add if I were to live on a boat again.
Social life was different. Our friends seemed less likely to just come over and hang out. But on the other hand, we got to host our friends on sailing trips and give them a very unique experience of the SF Bay. I can't speak to the experience of dating while on a boat, sorry :)
One thing to note: boats do come with a lot of maintenance -- saltwater has a way of destroying everything it touches over time. It was difficult to find people I trusted to come work on the boat without taking the boat to a boat yard (which meant moving out of our home temporarily), so I ended up doing most of the maintenance myself (shout out to my friend Eskil Olsen for selflessly spending his time helping on a handful of occasions!). I would only buy a boat if you are comfortable with learning how to fix it.
Economically we came out solidly ahead. We bought the boat for 39k, put about 13k of work into it (also a ton of my time), then sold the boat for 45k (after brokerage commission). Our monthly fixed expenses were about $500 (water, power, internet, slip fees). Considering a 2 bedroom in Berkeley would run at least ~2k+/month we probably saved ~30-40k over the ~26 months. That said, the time put into maintaining the boat was significant, and if that's not something you would enjoy, it could easily skew the value equation.
The social stigma was very manageable. People would be surprised and maybe slightly weirded-out when I'd first share that I lived on a boat, but as I'd share more I think people caught the vision. I think doing it with my wife helped normalize it. And once people were able to go sailing with us, I think they really got it.
We finally moved on land while pregnant with our second child. My favorite house-amenity is a dishwasher.
Finally, here's the (sold) listing for Chasseresse, the boat we lived on:
http://www.yachtworld.com/boats/1995/Hunter-336-3037385/Berk...