Hello Lindley,
The way we handle subscription orders is a little different from the way we handle more unique orders. Usually printing the shipping label is the last thing we do, so the system will send the shipping email, charge the payment method, and grant any PDFs on the order when that happens. With subscriptions we do what are called label runs. This means we print all the shipping labels for all the identical orders at once and then assembly line style pack them up, and ship them out. Because we print the shipping labels first you get the shipping email before your order ships out. That is why that shipping email will say, "is expected to ship from the Paizo warehouse by <estimated last day of shipping for the month>." Your order can ship out anytime between when you get that email and when we finish shipping out the months subscription orders. This month we expect to have them all shipped out by the end of this week.