Your price range and criteria are very similar to mine, however I am looking to purchase a boat years from now, after I retire from the Army and go through ASA 101-108. Anywho, that means to keep the dream alive, I have been researching boats, starting by going through this list:
Updated Offshore Cruising Boat List - January 2008
With all the researching and reading I have done, I keep coming back to anything Cape Dory, but I would prefer a 25D, Contessa 26 which this guy Bigoceans | Tiny Boat
even says is kinda small for a live aboard, also Island Packet 27
I don't hear too many gratifying comments on Pearson boats other than they are just "OK" but I find many for sale in my (our) price range so I am actively looking for owners to talk to about their offshore reliability.
Since I have yet to own a boat of my own, sorry I can't offer more than my research. Good Luck in finding exactly what you are looking for, my budgeting plan is to spend $10K on the boat and double the amount to refit her properly for singlehanded extended offshore cruising.
Good Luck and Take Care!