Gene Stafford, I will agree comes off as just dumb, because this guy has to be dense beyond belief to not guess that a guy like Milo is more apt to work him over at the very least, if not kill him outright in response to his macho bravado threats. I think the fault was not just the writing but a very bad acting performance that should have been dialed back a lot more.

I think Lilly, Roger, and Shirley can be blamed for being quite foolish, because, as it's been pointed out, they all knew that the people they were blackmailing were capable of murder. On the other hand, with Lanore and Gene, I think their being off-guard just goes to show that people like Milo and Brimmer seem too successful as businessmen to even entertain the idea of risking murder. Gene and Lanore might have thought these men unable to take such a risk. Also, I would consider Milo Janus as one of the most foolish murderers, because (if I'm remembering correctly) Lewis Lacey reveals later on that Milo hadn't really done anything criminal to begin with; that, even if Gene were to have exposed him, there wouldn't be anything to really indict Milo with. Of course, Milo wasn't aware of that before he murdered Gene.
And also, Eric, I actually think the writing and acting for Gene Stafford was quite good, but this is coming from someone who places "Last Salute to the Commodore" on my Top Ten list. (I understand that episode's not too popular with a lot of fans)

I've said it almost ad nauseum, but my problem with Lenore Kennicut is that she has almost a perfect opportunity for "counter-blackmail." In other words, she can promise Brimmer not to tell her husband what HE tried to do as long as he sticks to his "clean bill of health" about HER. And since she's obviously a smart person just like Brimmer, she should THREATEN to tell her husband instead of just telling Brimmer she's going to do that, period.

Incidentally, Robert Conrad and Philip Bruns starred together in an episode of "The Wild Wild West."

I just saw the bizarre horror film SLIENT NIGHT, BLOODY NIGHT, and Philip Bruns "played" one of those characters you only see in photos, because he's already a late character at the beginning. You hear a voice-over from the character because of a journal he left, but it sounds like a different actor doing the voice-over.