If the
DVC timeshare salesperson is selling you points at $130-$165 per point, they will put up with a little extra paperwork and laugh all the way to the bank. Plus, depending on how overboard you go, there could be some significant extra closing costs.
I really don't see any sense in going through all this for 100 points or less. The reality is that 100 points or anything less will generally sell very quickly on the resale market if the points have an attractive home resort. Even 150 point contracts tend to sell quickly.
It's a little amusing to pay $150 per point and then worry about getting $5-$10 more per point getting out. That's especially true if you are buying direct at a resort where you could buy resale for half the price (or less). Paying double going in, but worrying about your eventual exit price point is a classic example of being "penny smart, pound foolish," IMHO.
If you pay a huge premium for buying direct, and also finance, but use the small contract exit strategy as a partial justification, I think someone is really just kidding themselves. That person is really paying $200-$250 per point (or more) including financing costs and worrying about pennies getting out.
To me, there are two legitimate reasons why breaking contracts up into smaller chunks can be advantageous -- quickness to sell, and the ability to tailor your holdings to the size you want as your family's needs change. If you have a sizable DVC holding, multiple smaller contracts allow you do downsize more easily and precisely.
If you only own 100 points, selling 25 of them is not going to have much effect on anything; if you have 80 points and you sell 50, what do you have left? 30 points -- what are you going to do with 30 points?
But if you have 400 and can easily sell 100 of them that's a real plus.
There also may be some small advantage in being able to pass smaller contracts on to children equally, but of course that assumes the kids are going to want the ongoing annual dues obligation. If they don't, you're just "giving" them a financial burden.