Also keep in mind that - regardless of whether you buy resale or direct from Disney - SSR has 49 years of points remaining and all of the other resorts have 37. What that means is - if you do the math correctly - you will find that SSR is more costly to get into initially, but a little cheaper in the long run.
In addition to the per-point cost of buying in, don't forget to consider the annual dues. Those will probably amount to more that the initial cost over the duration of your ownership, and they vary a good bit from resort to resort - so research those as well.
The positives of buying resale are lower initial cost, lower initial cost, and lower initial cost. Resale prices
which get through Disney's Right Of First Refusal generally range from the mid-70's to the mid-80's, and what will pass ROFR varies quite a bit from resort to resort. You also have to pay closing costs in most cases, but remember that everything is negotiable in a resale.
The negatives of resale are that the process is slow, complex, and frustrating. Plan on 8-10 weeks from initial offer to actually being able to use your
DVC account. And the uncertainties of ROFR make it a very uncertain and stressful time. However, you will save on initial entry costs...probably several thousand dollars.
There are several positives of buying direct.
1. You are buying from a seller you know - Disney. A lot of people worry about the resale brokers - don't. The resale brokers are fine; it's the sellers you have to worry about - they are not always scrupulous.
2. The outcome is never in doubt - you know your purchase will go through.
3. You are getting 49 years of points at SSR, not 37, and that is not a trivial number. That's 32-33% more points.
4. Disney will finance your purchase, although you may be able to finance it yourself less expensively with a home equity line.
5. The process is a phone call. Almost immediately you are able to use your membership.
The obvious negative of buying direct is higher initial cost.
Here are links to a couple of other threads which may help you
http://www.disboards.com/showthread.php?t=778634
http://www.disboards.com/showthread.php?t=794010
Good luck!