I just did some rough math for myself on this. We have a 100 point SSR contract (in addition to 2 other small contracts at other resorts), and were considering adding on at SSR specifically.
Assuming we wanted to add 150 points in order to get the additional $8 per point incentive, and assuming we use a credit card with generous points values (e.g. penciling in 3% "back" for Chase Sapphire Reserve, for instance), we'd be looking at around $153 per point to buy direct. If I look at SSR contracts w/October UY (which is what I am looking for), there's a contract right now on
dvc resale market that is 150 points at $116pp, but that example $116 contract has no 2021 points remaining, meaning no points at all until October 2022.
The delta in purchase cost, then, is *roughly* $5,400 extra to purchase direct.
Now, factor into the direct purchase that you will receive 2020 AND 2021 points for SSR (assuming
DVC has inventory and you don't go on a waitlist until October), vs only receiving 2022 points for that specific resale contract, and you net some savings in only paying pro-rated dues (IIUC) for the 2021 calendar year. If you purchased on May 1, you'd then roughly owe 2021 calendar year dues around $700-ish (keeping the math easy), that you would not have to pay on the resale contract. That increase the price gap to $6,100, BUT you get 300 extra points to actually use. If you don't want to use those extra points but rent them out at, say, $10pp (after removing taxes, again the math isn't "real" here) then the difference in price goes down to $2,400 extra to buy direct.
If you're a family of 4 (like I am), and you were going to buy annual passes *regardless* of whether you were buying direct or resale, then the first year of your annual pass you'd save approx $2,000 that first year, assuming you are a non-FL resident (meaning you have to buy the Platinum pass), and that you're ok with the DVC-discounted "gold" pass as a substitute.
Now you're down to around $400 extra to buy direct. If you're sure that you'll want to renew your APs for next year and (even better) a few more years after that, the decision becomes easy. Even if you're not sure you want to renew your APs, if you're willing to gamble Disney will continue to offer that as a discount in the future (and who knows if they will), and think you might get APs again down the line, then the decision is still easy. If you think you WON'T want APs again, then the decision boils down to:
* Do you think DVC will bring back moonlight magic, and if so would you even be in a position to utilize it.
* Do you think DVC will keep the Epcot member lounge going on for awhile longer, and/or add more similar lounges in other parks, and do you think you can put a price on it?
* Is the extra $400 worth not stressing over ROFR, having the transaction be smooth, etc.
* Is the extra $400 worth having the ability to use 150 of your points to book at Riviera and/or any future hypothetical DVC resorts that will also carry resale restrictions?
You can see here that I'm sort of talking myself into believing that adding on direct at SSR *for me*, with *my use year* and with my plans around how I'd be using APs, that the resale SSR prices have now gotten high enough that a small direct add on contract is worth it. However, I would still suggest that for the most part even at current prices resale may be more cost effective.
I'd also suggest that overall if we hadn't already bought resale when prices were a little lower than they are, I might not be as interested in the DVC value proposition at all right now, but who knows for sure. *shrug*