I wrote something really long about all the down falls of living aboard but it was mean and probably more personal.
Here's the breakdown:
Don't do it if it's a means of cheap shelter - you ruin it for everyone and you will hate it and it will maybe even kill you. It's not cheaper than renting an apartment, under any circumstances, for a long time. Sell your boat and buy a camper van, live in that because it will not sink or smell as bad.
Only do it if you are mechanically inclined, willing to forfeit your weekends to projects and resent the boat ownership sometimes. There are rewards, but the juice isn't always worth the squeeze. Do it if you ask yourself, "If money wasn't an object, would I live in a house, apartment, or boat" - If the answer is still, honestly, "Boat" then I guess go for it.
Be aware that while living in rented places you don't ever really own the problems.. you pay rent and a person or company is there fix things and keep them up. When you own a boat and live on it, every single thing you are conscious of using until it breaks will become something that haunts you, and the only thing limiting your ability to rid yourself of those worries is money and time - the two things everyone struggles most with.
I'm happy living aboard, 8 months now. I've been through the boat sinking itself and through sleepless, uncomfortable nights during storms, and being afraid of pulling something apart to fix it because, "If I don't finish this all in a day, I have nowhere to sleep tonight" - Well, get used to it. Fortunately there's only so much to do on a 30' sailboat to keep it comfortable and functional and something to be proud of. I couldn't imagine you guys with like 55' ketch sailboats living on a mooring. Crazy.
I guess if someone only read the first and last sentence because it's not what they are looking to hear:
Save yourself, and don't do it. If that's enough to convince you then you aren't cut out for it anyways.
This is EXCELLENT ADVICE!!!
But, to answer your point of " I couldn't imagine you guys with like 55' ketch sailboats living on a mooring. Crazy." IMHO it is WONDERFUL!
We lived part of last summer, from early August until mid October, moored in Boston Harbor. With 65,000 pounds of mass, she didn't bounce around nearly as much as my neighbors' moored day cruisers. We have a built in Onan Generator. We have our own washer & dryer, solar panels, water maker, etc., so we were still comfortable and self sufficient.
Again, the bigger the boat the better the liveaboard experience is.