At that price range and size, you have a lot of options. But considering your intended plans, a newer but lightly-built boat might be marginal, even if it offers a lot of room below. I wouldn't want to forgo things like a skeg-hung rudder or a keel with encapsulated ballast.
There are a number of proven offshore designs that can offer very nice accomodation and modern and proven hull design, in a solidly-built boat say of late-70s/early-80s vintage, and for that price you could either get one cheap and have the upgrades done (professionally) on purchase, or buy one that already has new electronics/chainplates/rigging/sails.
Boats to put on the list:
- Kelly-Peterson (Formosa) 44/46 - Jeff_He's fav, major value
- Tayana 37
- Golden Wave 42 (lesser-know Perry design)
- Valiant 40
- Pearson 422/424
- Columbia 43 mk III (unusual suggestion, could save you a buck)
You will see all of the above in your price range on YW.