We JUST purchased a resale and got my membership card in the mail yesterday!
It was our intention NOT to finance and pay cash. So, we've been saving up for about 2 years. It's just my DF(iance) and I, and we figured that, based on our vacation habits and our budget, anywhere between 80-100 points was good for us. Buying direct from Disney requires a 150 point purchase, and the going rate is $95 a point (I believe). So, resale was our only option.
Now, let me tell you, if you're looking for a smaller contract (under 150 points), and they have one you're comfortable with, grab it. They don't come around too often on the terms you might like. The only way to get a smaller contract is if someone sells their add-on. Once you're a member, you can purchase add-ons directly from Disney for as little as 25 points (50 financed).
We chose OKW, basically because they seem to have the least expensive annual dues (or close to it). We wanted a WDW resort, due to the 11 month ressie window. We thought about VB or HH, since they're much cheaper per point, but we would never use those resorts, and we thought the longer window was more important to us. We've never even been inside any of the resorts. We stayed on site for the first time a couple months ago and the differnce staying at a REAL nice property outside WDW and the moderate resort we stayed at was tangible. No contest, Disney wins - you get to experience the magic 24 hours a day.
We called The Timeshare Store (we HIGHLY recommend - EXCELLENT transaction) and told them what we were looking for (80-100 points with none borrowed, preferably OKW) and told them to call when something was available. We were lucky to get a call within a week. We purchased at $73/point - 100 points. We didn't negotiate. I figured, if I go too low,
DVC will pick it up through ROFR, and what was I going to save - maybe $200? Over the life of the contract, it's nothing, and if I lost it over a couple hundred bucks, I'd be kicking myself!
I never thought of it as an investment, BUT (and this flies in the face of logic, if you ask me), the price for points has increased considerably since the beginning. One would presume, that the shorter the life of the contract, the less it's worth. Go figure. Fortunately, so long as Disney keeps the price artificially inflated (through ROFR), so they can sell the new resorts, we should be safe. There HAS to be a point, somewhere down the road, that the existing contracts get less valuable, since there will be limited time left on the contracts. But, you also have to figure, the price to "rent" at any Disney resort, say 15 years from now, is going to be much more. The cost for us will remain the same, so take that into the equation.
Anyhow, LONG story short... if you're paying (after closing costs) under the $85/point ($95/point minus the incentive), I'd just bite the bullet and pay it. If I were buying 500 points, I might try and knock off a buck or two. But, everything in perspective. In the long run, and if you can afford 500 points, what's a thousand dollars over 26 years (or whatever's left on the contract)?