Considering that the whole thing was, as an admiral once said, “a trap!”, Starfleet Intelligence should work a little harder on the “intelligence” part. Plan for this stuff, consider the possibilities, don’t send a high value target into the field with no backup (other than Worf, but I repeat myself. 
)
I see Chain of Command is considered “one of the best” episodes. I ask, how many have they seen?
Yeah. Using a technique that only one of Starfleet’s most prominent captains is the expert on is a pretty basic trick.
But the Picard versus Cardassian torturer scenes are gold (this was bad in the day when torturers were villains on TV)
Heh. Prominent for what, exactly?
‘Sir, remember when the flagship of the Federation stopped the Borg? Of course you do; Captain Picard got captured, and the most prominent Commander in Starfleet stepped in to get the win. That’s, like, Riker’s whole job: standing by to lead that crew to victory when Picard falls into enemy hands. Is he a shitty XO if you want someone to arrange shifts and schedules? Hey, you bet he is! But if you’re looking for trouble, you lock up Picard. So here’s my cunning plan…’
This. There is no way in hell the Admiralty should have sent a ship captain and doctor on a special forces mission.
And in an interview, way back then (when the show was still running, I think) she bemoaned the costumes she was forced to wear. The quote was something like “nobody’s boobs do that in real life”.
Star Trek management was definitely catering to the 14 year old boys of all ages in their audience with certain costumes (think of Seven of Nine’s outfits, which appeared to be spray-painted on and in one case did the actress actual harm).