Huh! I'll look into this.
Just to clarify: After the blood moon you said yes when talking to Milo and locked into his ending ? After the scene happened and the next day arrived you saved and then depression napped to the ending? But this triggered ending 5(?) and not Milo's ending correct?
Then when you are delivered to the main menu after ending 5, you loaded the save after having said yes to Milo only to have the same A/N appear correct? And because Milo's ending requires 2 days to complete there's a chance you won't be able to achieve his ending in the remaining time frame.
Also a quick question, ending 5 is the Gambling ending. Did depression napping somehow dump you into the Gambling ending?? (I'll have to check to see if maybe I forgot to take out some logic I was using for testing purposes.) I know Ending 6 (Beautification ending) can currently override the more 'canon' endings atm and it's something I'm thinking of adjusting.
I'll look into smoothing out the ending logic this evening and try to put out a new build. (I want to adjust how the gambling portion is calculated and I also believe that currently if you finish the beautification quest it locks you out of everyone else's ending which feels like it should be the opposite (beautification ending takes less precedence than Milo or Samson, since it's a 'joke' ending.)