Ill throw you a bone and provide a suggestion to one of the problems you have, but is also nearly as bad.
Instead of rolling at the opening of the window, which has a ton of problems that can lead to complications, roll at the end of the window. At the end of the window, Angry will be up and the turn in can be completed at that time and everyone can still stay and kill Skargus. This solves multiple issues with your suggestions, but creates its own list of problems that nearly everyone will hate.
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