Third special scene and eighth illustration are both automatically unlocked in Diego's route, so just skip back through Diego's route.
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I did skipped the whole Diego's route... I saw Which ones were missing... They didn't went to the gallery lol
As you said... Ren'py sometimes likes to mess lol it's like on my Tavern of Spear saves... Often the gallery bugs and misses some scenes... Then I need to play the save to get the scene again lol
I'll wait til the next update to see if it'll update... But really thank you for your concern Xevvy! It's nice to have the creator always in touch with the players! Thanks a lot!