There are so many things to consider in this equation:
1) As someone mentioned above....do the math....the cost of the points initially is SOOO much cheaper than the cost of maintenance over the long haul. SSR may look like a bargain, but there are some who believe (I know this because they have emailed me regarding this), that DVC will eventually stop being a bargain because the high costs of maintenance fees keep going up. Getting out 12 years early may be a blessing in 2042. I am not sure I feel this way (I don't worry about the future that much), but I do think it is worth mentioning.
2) Look at the cost of rooms each night. If you are looking at 2 bdrms and grand villas....you need to look at a couple of things. First, look at the cost per night of a grand villa at OKW, versus the cost per night of a grand villa at SSR....OKW is MUCH cheaper. The catch is...you pretty much need to be an owner at OKW to get those grand villas on a regular basis. However, the same is true of the 2 bdrms at OKW....they are cheaper. Also, look at the "standard view" options at BWV...they are on average 30% cheaper than the preferred/bwv rooms....basically, you get Epcot/MGM location at OKW prices. The grand villas, however are MUCH more expensive than those at OKW, and there are very few of them. However, my point is this.....the number of points you actually need is determined by how many points you need per night at the resort where you plan on staying most of the time. Both OKW and BWV standard are cheaper (most of the time) than SSR. This means fewer points, and lower maintenance fees (because you have fewer points).
3) SSR is NOT the only resort you can get via DVC direct. You can get ANY of the resorts. Usually DVC has all resorts available except BCV, but someone posted here that they got a 160 pt BCV contract last week as a new member. Just tell your guide which resort you want. Now, the "specials" do not apply to sold out resorts....they are simply $92 per point, but you can get them.
Whether or not a longer contract or location is more important is really a matter of personal choice. For me....vacations are too precious to stay in a resort that I don't care for, and "knowing" that I can get my favorite resort all the time (if I plan ahead) is the most important aspect for me. My money is important to me, but the precious few weeks that my dh gets off for vacation are even more important.....and, we don't get a second chance to have the "perfect" vacation when my dd is 4, or 5, or 6....or so on. You only get one shot to make great memories when children are little!!! I want my dd to grow up vacationing steps away from Epcot, with unlimited access to SAB, and what we consider the best resort on WDW property...BCV. We always say, "DVC is a really expensive timeshare if you are not 'thrilled' with your purchase....but, it is a bargain if you are!"
Do what works for you!!
Beca