It doesn’t do much to advance the story, but some papers do not have Sunday comics or even a Sunday edition, so a little bit of repetition is inevitable.
The Chicago Tribune dug up a strip from April 9, 2017. I have no idea why they wouldn’t have run the normal strip, but they might have chosen that one because it works as a self-contained joke, not needing strips from days before or after.
Maybe the Trib needs more lead time that they are getting. Contrary to popular opinion, the Chicago Tribune gets their strips from Tribune Content Agency like everybody else. It’s a separate company, although it may be in the same building.
He’s drawing from the description. If the outcome looks like one of the “tops” it’s because that’s the description. It would be useless for him to conclude that it looks like Flattop’s sister before even drawing it.
Pouch doesn’t know everything. The last we saw of him he wasn’t in a good place. Maybe he hasn’t fully recovered from that.