I bought a nice '94 Catalina 22 for $6K back in '06. Sailed it for two years. Did some minor maintenance and upgrades and with some elbow grease, bottom paint, varnish and wax made her look bristol. Sold her at the end of two years for $7K in three days.
- Really nice boats sell.
- Really nice small boats sell fast.
- Older boats have already depreciated. Make 'em look clean and you'll get your money back.
- If you go a little smaller you can buy something nice without busting your budget.
- Once you start sailing your ideas of what you want will change and small boats are great teachers.
This way you're on the water, you're learning and your budget's not busted. Small means less money, cheaper slip, less $$$ for bottom paint, etc.
If I was starting over today I'd do it the same way.
Best of luck in your search,