If I purchase a direct contract with October as use year, could I still get last year’s points? I’m confused on how to maximize the points they will give you.
Correct. What @Sandisw said above is true. You only get current year points when buying direct, along with future points as time marches on.
You may be able to get 2020 points when buying resale. Those points would have needed to be banked by the deadline. Those contracts are referred to on here as “fully loaded” or sometimes “double points” on the resale sites. There are restrictions to be aware of when buying resale.