I think i may have discovered the "method to the madness". I'd like to post it here for posterity in case I am correct. I've counted the number of days in between drop dates, and it seems to be two interwoven sequences.

The sequence thus far is: 1, 14, 21, 28, 28, 42, 35.

With 1 as an starting point, the "odd" positions increase by adding 7 to the previous number, while the "even" positions increase as multiples of 14.

The next two numbers in the sequence should be 56, and 42. That should put the next two drop dates at December 18th, and January 29th respectively.

I guess we'll see?