Awesome stuff, everyone. I really appreciate everyone's advice. To me, I consider all of you professionals, and you're making this a very valuable and fun learning experience for me.
@rgranger - I love Cats, but they don't seem to be too affordable, from my search so far. Amazing boats, but I'm also thinking a smaller profile (monohaul) would be easier to handle in and out of the slip (also cheaper slip fee, likely).
@gettinthere - Could you extrapolate on the battle against condensation for me? I can imagine how'd it'd be an issue, but I would love to hear more about it.
@dLj - What are some things I should look for in regards to structural integrity? How can I tell if a boat has been properly maintained? I can likely repair the engine, HVAC system, or electrical stuff, but no way I can repair a hull or other major external issues.
So here's my takeaway so far:
Pros - it's a good experience, could be fun, I'm used to small and "rough" living experiences, it's affordable compared to NoVa rent, chicks dig it (brownie points with the girlfriend??)
Cons - it's rough living, small place, could be very costly in maintenance and mods, requires skill and time on maintenance, no equity (the money could be potentially invested), I may not ever go sailing.
There's a certain romanticist notion I have that living on a sailboat would be an amazing experience. On the flip side, it would be lame if I never actually went out of the slip. I think I have my final major questions before hitting more research...
Lets say I buy a boat and the costs are equitable to renting an apartment. No equity gained either way, no money lost. I live-aboard for a year and decide I've had enough of the salt life and want to crawl back to land for awhile. How difficult would it be to get rid of the boat? What are the financial implications of this?
Truly, thanks everyone.