That’s a bug unfortunately. Don’t worry, though, there’s nothing useful (or important to an ending) back there. (It was just an outfit unlock.)
Cool, I think I have hit a wall with figuring out the remaining stuff so I'm going to check out a few of your other games later this week.
I noticed some events like the sequence where you 'break the clock' don't always occur - are these random or do they have specific flags in the game?
I also thought I had figured out that the prisoner outfit triggers the day change, but it doesn't seem to do that this time round - something more to it?
Breaking the clock has a very specific meaning and reason it appears, but a lot of different ways to trigger it. It doesn’t have anything to do with any of the endings, though.
As for what triggers the day change, I don’t want to say too much. Just be sure to listen to the man in red whenever he appears. If he gives you a warning, be sure to listen.