@FaintlySorcerous , seconding this. I know you're pushing word-count if you treat 299 as the limit, but the plan lasts less than a day, I think it's fine to forgo the brevity bonus in favour of a more detailed plan.
I'll also note that I thought the section below from your original plan was really nicely phrased:
In that it makes clear that we trust him to be honourable according to his own definition, but we don't know if that includes not planting kill switches in us (or if his honour is meant to include that, guilt-trips him about it or at least gives a concrete example to use as a reference for why that was fine but kill-switches wouldn't be). Any particular reason that got cut?