Re: New to the sport
I'd start with a search here to get some thoughts on cruisers, then go to yacht world and sailboat listings and see what looks pleasing to the eye and what my spark your interest.
Next; walk around some marinas/yacht clubs and ask for in put.
I would think in your price range that you should be able to find a decent 70's to 80's cruiser in the 25' to 30' range. Think small! It's the best way to start. Maybe even a trailer sailor that you could take elsewhere (inland) and explore. (Catalina 22')
After all of that...(months and classes, 101)
Find a sailboat broker that you like and can work with and let them know where your interests lie. DON'T do it on your own. It doesn't cost you anything. Surround yourself with people that know. In addition; find a surveyor that is not recommended (per se)by your broker. I mean, find a surveyor that can be impartial.
I think you are starting the right way. Make a minimum investment; if you like everything, you can always upgrade ; if not, sell out.