Edit: literally five minutes after i posted this, i saw the scene. i guess it's subject to the RNG?
I don't think so. While plenty of stuff is dependent on RNG (like whether or not the dreams trigger), reading the code it would seem that it's just that, for some reason, the dev made that quest only trigger on days 2, 4 and 6 (it's an array, I don't remember if it starts on Sunday or Monday). So maybe you just checked on one of the other days?
Then there's also the fact that sometimes the characters aren't where they're supposed to be, which obviously screws up everything. I haven't noticed that in this update, but I know it happened with Amelia's first quest step in her bunker in the previous one. It would just be empty all day long.
All in all, I find that those periods of waiting for a "few days" that end up being over 2 weeks are annoying and one of the most negative parts of this game. Especially when the quest info doesn't really help you know if there's something missing.
The proper way to do this would be to also include the info on what else needs to be done (like what happens in some of Uma's quests), how many more days you need to wait and even if some other quest needs to be advanced.
Maybe I can add that if I ever make my quest changer mod.
Sadly, without it, some quests end up being just a matter of "brute forcing it". You just keep trying it regularly while doing other stuff.
Anyway, good to know you managed to advance it.