I may have misunderstood this question so let me know if that's the case. When you roll a die after rerolling the prompt, this is outside of your challenge roll. So it doesn't matter if it was a success/failure or critical success/failure before. If you roll the same prompt, let's say someone dug up a scandal, and last round it was a crit success which everyone believed you and that someone was now in jail, and this time, you roll an odd number, it takes a bad turn. Maybe the person in jail was assassinated and people thought you are the one that ordered the assassination. Now you roll the resolve the prompt.
And don't worry about the questions! It's not that I don't want to answer questions but more like I personally feel insecure about the time travelling rule because I now feel like it's too convoluted 💀
God, your LIs are depressing 😭😭😭And full of plot twists lol.
This isn't a potential LI! But they're now in the pool of potential LIs if you roll the one where a minor character becomes another LI.