I'm going to give you a dissenting opinion. IMO it essentially never makes sense to buy small contracts of the same resort and same use year at the same time simply for the possible insurance of having to sell later unless there is little to no cost in doing so. If you think you're going to sell later, just buy less or don't buy at all. However, unless you find a single seller selling multiple contracts that you can buy as one, there is really no way to meet those requirements resale. Either you pay more retail for the option (and give up the fixed week option for GF) or you pay more with extra closings and a higher pp cost. On two 100 pt contracts you'd talking an extra 10-15% more or around $2000 additional. Now if you want to buy some now and some later or two different resorts it MAY be worth it for some but likely not for most. There is a size where one really should break it up if possible but it's not reasonable until one gets to 300 or more so that each contract can be at least 150 pts.
I'd say better just to buy a few less points say 150-170 instead of 200 in that example. IF one chooses to buy 2 resorts and are not already very experienced with
DVC, you buy one then see how it goes for 1-3 yrs rather than 2 now.