Your circumstances and motivations sound similar to mine a year ago (26, traveling job, didn't want a house, love the water), and I've been happily living aboard a 30'er since last fall. When all was said and done I spent about 15K to have the boat in the shape I wanted and in its slip, with help from a small loan from a local credit union. Since then I've nickel and dimed myself into more expenses and sweat labor, but it's out of love so who's counting. . .
I was going to add a few things about the lifestyle but it went and turned into manifesto length. C'est la vie, make some popcorn. First with the general/financial:
--The insurance suggestion is key. I've found that marinas want proof that you're covered before they'll let you moor there. I also found luck with BoatUS where others wouldn't cover me based on my lack of sailing experience (we had power boats growing up too but it didn't translate over).
--Also to echo another comment, liveaboard moorage can be hard to find so it may end up being your biggest headache if you want to move the boat around much. In Seattle there's a 10% liveaboard limit at all marinas, so I had to sublease someone else's slip for 6 months and make friends with the marina manager to get my foot in the door to my own lease. I recommend this approach to cold-calling marinas -- many have bulletin boards showing sublets or you can keep an eye on craigslist too.
--The bank told me that if I'd wanted to buy a house instead they weren't sure they could support it based on my lack of long-term credit history (no car payments, but many years with a credit card). It's interesting that one needs to make large purchases in a certain order - so in a sense I feel like I'm not only circumventing the system, but improving my chances to buy into it later if I wish.
--A good marine survey is worth its weight in gold. The $400 I paid for mine identified rot in the floor timbers that cost me around 8K to have repaired. Because I knew early, I was able to negotiate with the seller in such a way that I ended up paying exactly what I wanted to spend on the boat.
--Boats take a lot of maintenance, though I can't compare it directly to a house. My list of little tasks and improvements has only grown the more I understand my boat's design and systems, no matter how many evenings and weekends I dedicate. That said, I find it very satisfying to have picked up a number of new skills (sewing, mechanical, plumbing, electrical, etc.) and I'm a constant forum lurker in search of more knowledge. Be prepared for the boat to take lots of your time.
Now on to the saily stuff:
--I'd only been out sailing with family friends a few times before taking the plunge. As one of them put it, "It only takes you about 2 hours learn to sail, but you'll spend the rest of your life learning how to sail correctly." It doesn't have to be a barrier to your entry if you're willing to be a slave to the details and be smart about the progressive risks you're willing to take.
-Books are good. Having a partner is good (for reasons already mentioned which I second). Being a patient learner and teacher is good. Having a GPS
and charting program is good. Having someone show you how to maneuver a sailboat into the dock is very good (it surprised me how differently they turn compared to power boats and how that impacts your timing/choices). All the rest is just pulling on ropes until you like what you see. I say this being a mostly fair-weather sailor, so apply the grain of salt here.
--When I was still in the considering phase, my best friend put the question to me this way: "Suppose you buy the boat and it sinks within a year or you just don't like it anymore. And if in the end you lose that money and have just **** in your hand, will you still be glad that you chose the experience?" So far I'd still say yes, and the switch from apartment to moorage fees cut my rent in half so I can convince myself that it's paying itself off. Math is fun.
--Living aboard feels surprisingly normal within a short amount of time. Now I have no problem plodding up the dock to the shower in my bathrobe, I've gotten used to rearranging the whole boat in order to get at that one thing you need, and I've even grown to like the slight boaty smell. I'd find it hard to share, but 30' fits me very well.
--Things that suck include ironing your clothes, trying to get intimate in a low-ceilinged v-shape bed (sorry, true), the fridge that's never quite cold enough which leads to lots of soup, sandwiches, and pasta onboard, and finding a place for shoes and tools (I just use the head as storage when at port). But hey, as long as I can boil water and use the Internet, I'm largely happy because I come home to a freaking boat!