It's not possible to pick up items that spawn on top of the stairs by double-clicking them (e.g., in the Rogue Gold challenge). You can still pick them up by clicking the "pick up" button, of course, but it's inefficient and inconsistent this way. (You're never able to use the stairs by double-clicking them, anyway, so there's only one reason to double click on that tile.)
You get the "barely win" prediction when both you and the enemy have death protection (both DPs will be used up but you won't win).
The Rogue Gold completion dialogue refers to something the "old orc" said (I was playing an orc, natch). The boss was a human-type, though, and I don't see any other references to an orc telling you something in that quest line. I may have forgotten, though, seeing as it's been a little while since I did the bronze and gold challenges).