Context only goes so far.
Absolutely, context isn't going to magically make shit that's not ok, ok. But it still matters though. Both TOS episodes you bring up are at their core, Prime Directive episodes. The whole point of the Prime Directive, is an anti-colonial message. Spoken pretty bravely in the middle of the escalating Vietnam War, where our leaders had convinced themselves and a good chunk of the population that it was righteous and necessary to side with colonial oppressors and dictate the destiny of other peoples for them.
The Omega Glory's scenario is one where another Starfleet captain (who we repeatedly hear are the people with the most upright and impecable character) sides with the Kohms because he's in too deep and sees only their POV. He spends the entire episode trying to arm them and help them fight. Because he shares a more kindred connection with the more technologically advanced and settled Kohms, and sees the Yangs as the instigators in their conflict, as they initiate regular lethal raids on the Kohms. The whole reveal that the planet is a mirror of Earth, and that the brutal and ignorant Yangs are actually Americans, was not necessarily meant as a "noble savage" allegory first and foremost but to show domestic viewers that our culture is not inherently superior to others, and that we can face dire consequences/extinction if we continue down the path of aggressive warfare and forget the foundational morals of our Republic. A good message, delivered in an unfortunate, short sighted manner.
Paradise Syndrome is absolutely racist for sure. But mostly in that you've got white people misrepresenting indigenous cultures and absolutely bathing in racist tropes. (Same with Code of Honor -- which has way less of an excuse, made two decades after TOS and the Civil Rights Era, among active protestations from people within the production.) And yet if you remove those tropes and colorblind the script, there are still Prime Directive stories here. If Paradise Syndrome was instead about Kirk landing in say, a facsimile of colonial New England, and him and Miramanee ended up persecuted for witchcraft at the hands of a bible thumping mob, I don't think anyone would have a problem with the episode (or at least this problem) and it could still have all of the same plot beats and story themes. The core of the episode -- the personal cost of becoming emotionally entangled in a place you shouldn't be -- is in spirit very similar to other beloved episodes like The City on the Edge of Forever.
I'm not saying anyone should forgive or ignore the shortcomings of these or any other episodes in old Trek. It's good we talk about these shortcomings and how things have and have not changed in the last 60 years. But context always matters. These episodes were written 60 years ago, when our society was just beginning to have these kinds conversations in public, in a modern media environment. Written by people raised in a deeply racist, segregated society who were trying to be better, but still ultimately shaped by their surroundings. Maybe it's the history major in me, but we're far enough removed from TOS that I find it natural to look at it more dispassionately and compartmentalized. In all of the ways TOS was ahead of its time, it was still ultimately a product of its time as well.
I think for me, the most insulting and unforgivable episodes of TOS are episodes like The Way to Eden -- which is not trying to say anything meaningful or progressive, but is really just a tone-deaf chastisement of the counterculture movement, and the idealism/impulsivity of youth. There's no real additional context you can give there that can excuse that. It's just purely old people being close minded and talking down to their audience, ending up on the wrong side of history, counter to what the rest of the show ostensibly stands for. Or Turnabout Intruder. Which, under even the most charitable of readings, is essentially saying yes, we know women are just as capable as men and given the short end of the stick by society, but please stop being hysterical and upset about it. Gross.
