I tried a couple of different ways of managing points, but the easiest for me by far has been to set up a separate "cash" account in Quicken for each set of points. (It doesn't matter in Quicken if you are tracking points or money.) For example, you might set up one cash account for AKL March points and a separate account for BWV March points.
Then it's a simple matter of entering the dates you receive the points every year, and the number you receive. When I make a reservation, I always enter it (in the account I'm removing points from) as of the date the reservation starts, and of course note the type of reservation it is and who it's for.
Ex: 10/2/2016 AKL Studio, 2 nights, Jambo House, Mary and Sam.
Then it's always easy to see where I stand vis a vis borrowed points, remaining points, etc and when they will actually be used.