You're not supposed to kill the guard. If you have found some fel shenanigans by which you can kill the guard, then kill the roaches, then I will need to be informed.
As for 1S, is it the slayer maneuvering you're having issues with? I seem to simply have some affinity for it and have this nasty tendency to assume that it is this simple affair because I am ignorant or something.
The main difficulties in that room are, I'd assume..
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×Getting the slayer into the box and you out.
Then.
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×Figuring out how to connive the slayer into killing part of the rattlesnake for you.