Thank you so much for all the praise!
To answer your question:
It depends. Sometimes we update just the images themselves, so the progression stays and you don't have to replay anything (Like in cases of Freja and Reina). But most of the time we also rewrite the script on top of that (Like in cases of Sonya and Seraphina), so in this scenario you do have to replay the updated route to get the scenes in your gallery (It's worth it though, since in this case it's a brand new experience).