AH, I MADE A mistake. It was Ending 2, not Ending 5, so sorry! They kind of look like flipped versions of each other, so I guess my brain got confused... Very sorry for the mistake!!
To clarify what happened:
- Blood moon, said yes to Milo, locked into his ending
- Said NO to the depression nap option **immediately after** the conversation with Milo, so I could make sure I didn't miss anything I wanted to do
- The next day, looked all over the map, was satisfied I didn't miss anything, so I did some random money making task (I think it was the last step of cleaning the backyard?)
- Made a save when it prompted the depression nap the next day
- Took the depression nap, got ending TWO (so sorry again), so I reloaded my save figuring I'd missed something
- Loaded back in at the casino (not where I had saved), a bit confused but the day was the next day so I figured the game was treating it like I had said no to the depression nap
- But then Milo was at the backyard again, and was repeating the same dialogue I had already seen.
I hope I didn't cause you to needlessly look into the gambling ending with my mistake ;v; Thank you for the quick response, I hope my clarification helps...!