So, after plot resetting for Diana for a couple hours, I saw Cole walked past what looked like a good placement while the game was starting up. Should I start the game as my mayor to get her there, or would she stay in that spot if I started as a new save file? I want to double check, but I'm scared of loosing her placement.
No don't. Sometimes when the game starts up it's that way when you would start a new character, but it's not always accurate. There are chances or not that her house plot will be in that location if you start with a new character.