We bought at SSR in 2003 and haven't regretted it for a second.
We looked at resale, but in the end decided that the 50 year contract at SSR and the location at Downtown Disney suited us best.
We had our first trip to SSR in October/November last year, staying in a 1 bedroom. The whole place was fantasic, really high quality.
One thing is to have a good idea if you want to buy SSR from disney or buy a resale contract, as once you do the tour there is a time limit on whatever special deal they are offering at the time. I can't remember how long it was.
We decided to buy when we returned home and paid by credit card. They posted all of the paperwork to us to sign, which was very clear and easy to do.