Part of the trouble is that each resale must be evaluated on it's own merrit. You must look at how many points, how well it fits your needs, what closing costs, what maint fees you will need to pay and what the points situation is for that contract.
In general, I'd think you could get a smaller OKW contract with good availability for $61-62 per point plus closing and a prorated closing cost. While I personally think the use year is important for some, it's not important enough to walk away from an otherwise good deal. Remember that the difference is $62 vs $65 per point on 200 points is only $600, not enough to sweat in the long run. You need to decide what you want and at least how you are going to evaluate each offer so you can be prepared to move when the time comes. Cash or financing will also need to be available at or right after the time your offer as accepted as time to closing is usually only about 6 weeks or so.
DVC charges maint fees on a calendar basis so what is "fair" to reimburse will vary based on points availability and use year.
I'll give a couple of examples using 200 points at OKW with a December Use year. I'm going to add or subtract $10 per point for points availability or not and assume we're closing somewhere around 1 July, 2002. I'll assume a basis of $65 per point for discussion purposes. These are my views and ways of looking at this so others may vary slightly. I'm trying to portray a neutral situation realizing all is negotiable. We'll assume $450 closing on all paid buy buyer. I'll also assume buyer can use or bank all extra points. If there were points you couldn't bank or use that would expire, that would make the contract less desirable though you might still be able to rent them.
Example 1: 200 points in the 2001 use year (good until Nov 02) but no banked or borrowed points and all 2002 points there come Dec. $14094 ($13000 +$450+$644 maint fees) and you'd be getting a freebie on 1 month of the 2001 points.
Example 2: 400 points in the 2001 use year (good until Nov 02) with 200 banked points from 2000 and all 2002 points there come Dec. $16094 ($13000 +$450+$644 maint fees+$2000), I wouldn't pay extra maint fees on the banked points as that's already figured in the $10 per point value. The reality is I'd value the banked points less because of the shortened life so you'd need to see what they're worth to you. I'd put the value at more like $15000.
Example 3: No points in the 2001 use year, no banked or borrowed points and NO 2002 points there come Dec. $10094 ($13000 +$450+$644 maint fees-$4000). Again the $10 per point adjustment takes case of the current and next years point deficit including. Again, you'd be unlikely to get anyone to actually take the real value since it would be so much different than what they paid and expected so you'd likely need to move on to another contract.
Specifics will vary with each individual contract and situation. Sometimes if something just fits, it's better to take it and move on and not keep worrying about $300-500 you might save later. I would never tell a seller this but you need to know that any reservations not completed before closing will be cancelled by DVC and the points returned to the owner (buyer). It's possible to pick up points in this way. Of course in many situations the fair thing to do would be to attempt to reserve again the cancelled reservations for the seller.