Is Buying Direct Worth it in my case?

Just remember that they can keep the annual pass discount, but the delta can change. Others correct me if I'm wrong, but I believe the AP discount has historically been closer to $200 PP rather than the current $400. The $400 difference really just stemmed a few months back when they increased the price of the platinum but not the Gold. If it goes back to $200, your break-even time frame would double.
Before the last increase the Gold AP was $609 and the Platinum AP was $894 so the delta was much smaller (so closer to $300). That's because the Gold only went up $90 while the Platinum went up $225. This lines up with the date based tickets were Christmas and Easter had some of the highest adjustments in prices (though they catch much less attention now cause of the date based pricing). So I suspect we see differing degrees of price increases on the APs now they went date based pricing for normal tickets. Remember DVC members are minuscule number of Gold AP holders (compared to Florida Residents) so likely don't weight much in where the Gold AP should land. They really just want to deter Florida residents from going over Christmas and Easter and crowding the parks (so I suspect the delta will always be something that isn't too much to ignore). If we go back in time we see the Delta get closer to $200, but that was over 3 price increases so the trend of the Parks Division (setting the prices not DVC) has been to increase the delta (again probably to deter Florida Residents).

As long as Disney makes more money on DVC members going into the parks (spending on Food and Merchandise which is where the Parks Division makes most of its money) there will always be some incentive to give DVC members some level of entry discount. The question is what does that discount change to. Disney isn't making money on the rooms from those members anymore so enticing them to use the parks more often is advantageous to their bottom line. Plus APs make it easier to justify more trips which make it easier to justify for adding on. I'm sure there is a lot that goes on in their decision to offer the AP discount.
 
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Saratoga Springs isn't selling for $110 on the resale market. The highest priced listed contract on Fidelity is currently $103/pt and most are in the $90s. Contracts can be easily had in the $90s. I paid $86/pt (contract was listed at $88/pt) with a 55% of the 2019 points available - I banked them and just used them (along with all 2020 and some 2021 points) for a July 2019 reservation.
You can find a contract in the $80s if you look around.
 
Aknotts66 you guys sound like you got your act together. I would say to buy that direct 100 point Rivera
DVC now. Then add resale in the future. I would say just understand what Use Year means before you buy.
 

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