There are a lot of reasons to buy direct over resale. Everything comes at a cost. Resale is giving up ease of purchase, it's giving up some perks, and it comes with restrictions. So nothing wrong with buying direct...
Which resort to buy based on your variables:
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Point chart is kinda irrelevant. If you could get a room at POP Century for $200, but a room at Grand Floridian was $210, would you choose POP Century because it's $10 cheaper? The same works with
point charts. Rooms at Old Key West are fewer points than rooms at Grand Floridian -- But the rooms are also cheaper when paying cash. So while you should certainly consider costs, remember you get what you pay for. The nicer and newer resorts, the bigger rooms, cost more points.
-Location -- Nobody can answer that for you. Want to be walking distance to Magic Kingdom? On the monorail? On the skyliner? Close to Epcot and DHS? Walking from Epcot? It's an entirely subjective question.
-Value/incentives -- The best incentives are always at the newest resorts that have millions of points to sell. So that's Riviera and Grand Floridian (due to the expansion of
DVC there). The direct price of a sold-out resort can be quite a bit inflated.
I realize I probably didn't help you much. But my advise is mostly:
- Buy where you would want to stay, as you'll often be stuck there.
- In terms of value, look at is based on your subjective preferences. Okay... 150 points.. maybe that's enough for 8 nights at SSR but only 6 nights at Riviera. (guestimate, I didn't look it up).. so would you rather have 8 nights at SSR or 6 nights of Riviera per year?
-In terms of value, especially if buying direct, AVOID the 2042 resorts. Financially, paying direct price on the 2042 resorts just doesn't make mathematical sense. It would be cheaper to pay cash every year.