Read "advice on books for the VI" on the learning to sail forum. My opinion of your plans is summed up in my response there.
You could certainly find an appropriate boat in that price range if you are willing to go old, get dirtly, and don''t mind sanding and grinding. This would mean forgoing most luxuries - like on board showers and hot water. The old Pearson Vanguard pops into my mind and I am sure you could pick up a decent speciman in this price range. Be sure to budget for a new set of sails. Even cruisers need decent sails to sail safely.