This has been placed on https://www.drupal.org/node/2634778, but since there is no any reaction there yet I thought I'd have better chances here on Drupal Questions.
This has been tested well on a clean Drupal Commerce setup:
If a product configured with prepaid license billing type (see different billing types on https://www.drupal.org/node/2127603) is checked out, then everything works well - Drupal Commerce creates two orders: one already processed and one for the next billing period with the "Recurring: Open" status.
However, if a product with postpaid license billing type is checked out, then Drupal Commerce creates only one initial order that never recurs. What is interesting, if a postpaid product is checked out together with a prepaid product in a single order (just to get an order with "Recurring: Open" status created) and then if prepaid product gets cancelled, then the postpaid one keeps recurring successfully.
At the same time, if "Example payment" is used instead of "Commerce Stripe" as the payment method, then both pre and postpaid products recur without problems. Which makes me to believe that something in Commerce Stripe is not triggered when postpaid product is ordered.