Here are a few points to consider: 1) I think it's best to buy where you would most like to stay. For me, I love AKL and it just wouldn't be the same anywhere else so that's where I'm buying my points (resale). If it truly doesn't matter, buy SSR and save money. 2)If you know what resale does and doesn't get you, then you should have no reservations about buying resale. Even my member guide told me he would buy resale if he were me. I am buying to stay at a DVC resort. Period. I'm not interested in using my points in any other way. Just use a major resale broker to safeguard your investment. 3)As for how much to offer? Offer what you think it's worth. Check out the ROFR thread. I made MANY offers before I had one accepted. In fact, I offered $61/pt on a AKL contract listed at $75/pt. It was the last contract left to make an offer on through Fidelity that met my criteria. The sellers agreed to my price without so much as a counter offer. The right contract at the right price will come along if you're patient. (Mine still has to pass ROFR though!) Do your research and make sure you are happy with your purchase! Good Luck!