Something more fun to bump this thread and talk about.
Startrek.com made a post ranking their top ethical quandaries and moral impasses faced by the Star Trek command crews over the years and series...
Looking back at some of the times each captain found themselves at a moral impasse.
www.startrek.com
Looking over the list, they substantially overstate the situation Georgiou faced, it was very clear that Burman's "advice" was unsound and not based in anything more than Burman's own issues with the Klingons. Also, as the article notes her decision ultimately changed nothing.....and as the article
doesn't note, she followed up that inconsequential "choice" by booby trapping the corpses of enemy soldiers, which is a bona-fide war crime.
In the Pale Moonlight is probably the most interesting one on the list, because it's one of the few that didn't have the captain make the moral choice or find a third option. Should go higher on the list.
Can't speak to Pike's thing, I quit watching STD.
Tuvix was a predictable choice for this list, though I think "Nothing Human" is better, because the questions Nothing Human raises are a lot more real than those in Tuvix.
For Enterprise....well, it wasn't Dear Doctor, thankfully, but "Similitude" still felt very weak as an episode.....though Enterprise itself was also kinda weak, so there's that.
"I, Borg" was pretty good at the time, but later media that established that A) the crew's plan would never, ever work, B) Picard clearly changed his mind at some point about his choice here given the events of STFC, and C) They really, really, really should have Hugh take one for the team for this one. The phrase "needs of the many" comes to mind.
And then of course there's City on The Edge of Forever, which oddly had them do exactly that, though frankly the casuality rate of Kirk's love interests takes a lot of the sting out of this.