I lived aboard a 60s-vintage 40-foot Owens for the better part of a year... the owner had lived aboard and traveled a lot in it with her little dog for 15 years(!!), and when she moved off it, she rented it out to me as if an apartment.
Initially, there was hope that I'd be able to take it out sometimes, but her plan to get one of the prop shafts fixed fell through, so it was moored the whole time.
But I loved it!! Cold as hell that winter (and very, very damp!!), but I did OK at night with many layers and a kerosene safety heater, and on sunny winter days the galley was like a greenhouse.
I had shore power, telephone (I had an extension on the bridge so I could answer "Bridge!" if it rang while I was up there), only two other live-aboards in the marina... it was peaceful, and it was a great place to throw a (not-so-peaceful) party. Great view of NYC from there, too(marina was near Liberty State Park). The marina was off a canal off the harbor, so no wakes, swells, or wind-driven waves ever... she would just head back and forth a little in the wind sometimes; kinda nice, actually.
And "Aphrodite", as she was named, was a babe magnet, even tied to the pier. Fun.
Only PITA, really, was getting water into the tank in the winter when the marina shut off the water taps on the docks and I had to haul the hose over to the laundry room. That sucked. There was no storage tank for "brown water" t empty, though, thank goodness (yeah, I know it's illegal most places, but I think the marina ecosystem absorbed the poo of only three live-aboards pretty well).
Good point in this thread about simplifying your life: I had the boat pretty well fluffed (even a fish tank!), but I had to get rid of a lot of stuff to move in there, and had to keep everything in its place or I'd be up to my eyeballs in my own possessions in no time. But it was easy work to tidy up, I loved the ergonomics (perfect space for one bachelor), all that nice wood around me, storage everywhere, and that little galley kitchen was my favorite kitchen ever- really enjoyed cooking in there.
I suppose if you live aboard a boat that travels, things could get a little hectic, not to mention expensive. But as a living space, a boat can be a very cool sort of cottage.