Joe, as an example, if you wanted to stay for at the OKW in 2014 during "magic season" you'd need the following number of points at $5.34 per (based on 2013 fees, which looks like an increase of 2.7% over 2012):
108 points for a studio (376 sq feet) ($576)
222 points for a 1 BR ($1185)
296 points for a 2 BR ($1580)
477 points for a Grand Villa (2547)
http://www.wdwinfo.com/disney-vacation-club/OKW-Points.shtml#okw2014
If you can find time during the school year to get away, you can go for significantly less. In September, January and first part of December, a 2BR villa costs about the same as a 1BR does during peak time.
There are a few sites that list resales. On 1 site I found the selling prices ranged from $67-$73 per point for OKW. So taking the average of $70 per point, you could buy:
100 point contract for $7,000 + $534 per year (not enough for even 1 studio per year during summer)
230 point contract for $16,000 + $1228 per year (gets you into a 1BR with 8 points to bank, or 2 weeks in a studio)
300 point contract for $21,000 + $1602 per year (gets you into a 2BR villa during the magic season, with points left over during slower seasons)
Obviously
some of/all of/more than the purchase price, closing costs and carrying costs can be recouped upon your own resale. As a seller, you're sort of protected by Disney's Right Of First Refusal creating a floor for how low these contracts can be sold for. As a buyer, the same floor comes into play on how much you'll pay.
So if you wanted to stay in a Disney Villa and the only think keeping you from doing so, this could be the way to go. You could break these points into smaller trips, smaller accomodations, different times of year, villa this year and studio next...the options are endless.
My view is that it is only a good deal when compared to paying Disney rack rate.