The best thing to do is visit the DVC kiosk and tour. It is super low pressure and actually kinda fun.

Basically, for us, we looked at available properties when at WDW last May (AKV, SSR, and GCV) and went from there. We knew we wanted to buy from Disney; you can also buy resale. We toured the SSR and DH loved it. He loves to golf and he likes the condo style set up vs high rise hotel room. We got lucky too as SSR was the least expensive to buy into at the time and the maint. fees are not bad. You can finance through Disney as well. We toured, asked a TON of questions, sat and milled it over, asked more questions, then paid our money.

I would be happy to answer any $$$ specifics via PM.