JayTar
Idea briefcase
That is why I would rather bring him with us then leave him with the waitress. While we seem to have at least somewhat convinced her, that doesn't make her a reliable ally. All we know for sure is that she isn't willing to stand up to us. And considering that we just killed her, that may be due to fear as much as anything.I'm a bit worried if we leave Robert alone he might get murdered like last time. And there's a chance Oliver ends this loop for good. Or run afoul of the Hound. We're about to head to a dangerous encounter ourselves.
The Waitress although misguided doesn't seem like a bad person, I'm hoping they'd be alright together under the sight of the guards and other staff. Excellent ideas btw, updating my vote with the questions.
I suppose if we make sure to tell Robert to stick to areas with plenty of witnesses that might be okay.