<font face="times" size="+0">I'm going to attempt some convoluted math here.

(I call this convoluted because IMO there really is no way to truly valuate which one is "the better deal")
Assumptions:
Pay cash for your purchase (no financing, so no interest costs)
Contract size = 150pts
SSR price = $85/pt
BWV price = $74/pt
Resale closing costs = $450
SSR remaining life = 50 years
BWV remaining life = 38 years
Dues Increase Rate = 5%
Own
DVC for entire lifespan
General Inflation is Zero (yeah right)
Capital Costs:
SSR = $85 x 150pts = $12,750
BWV = $74 x 150pts + $450 = $11,550
Dues Costs Over Lifespan:
SSR, 50 years of dues, forecasted out at 5% increase each year = a whopping $125,881
BWV, 38 years of dues, forecasted out at 5% increase each year = a whopping $72,239
Total Cost:
SSR = $12,750 + $125,881 = $138,631
BWV = $11,550 + $72,239 = $83,789
Divide Total Cost By Years:
SSR = $138,631 / 50 years = $2,772/year
BWV = $83,789 / 38 years = $2,205/year
BWV is thus "cheaper" using this "math".
Okay, I don't really agree with the concept of the above math (besides, it's quite flawed w/ no TVM accounted for), but I've seen a lot of people calculate it this way, so in anticipation of that, I thought I'd lay it out first.
Basically, you have to remember that the big bulk of your costs of owning DVC will be your dues over the lifetime of your ownership. So, obviously SSR will be more expensive.
I think you can't dwell on this kind of valuation too much, and other factors should be more important. Things such as which resort do you like better, which resort will be better for your family, etc. Also, how do you know your family's future generations will even WANT to vacation at WDW? There is no way you can know that.
I'll post back as I think of other factors, but that's just off the top of my head.
Hope this helps!</font>