Earlier posts go through it in more detail but the sum of where I'm at is that TNG is a naff conservative-leaning show and VOY is its soft reboot so carries the same flaws; VOY obscures this somewhat by being kinda off the rails and uninterested in its own story, but only somewhat. In truth, this isn't really much of a problem: I doubt people are being radicalised by these shows into advocating for the retirement of democracy in favour of an interstellar military.
Most people are aware of the general consensus that Trek is "progressive", so they think of these shows as progressive, and (from my vantage point at least) it seems like the culture has run with that. Meanwhile, there's this eternal and tiresome battle about whether Trek is 'conservative actually', and this battle never gets anywhere because no one agrees on any definitions and no one agrees on what's actually happening in the Trek universe.
So... here's my take. I borrow the Innuendo Studios approach of "conservatism is the ideology that maintains some kind of aristocracy via whatever means are available". In short, there's a ruling class and that ruling class has clever ideas like "the market" and "hereditary titles" that keep it secure and exclusive, and a conservative is someone who supports these ideas because they either fell for the propaganda or are/expect to be part of the ruling class.
To be anti-conservative is to work or want to get those structures ripped up because they suck.
And to be 'progressive' is, for the sake of this infodump at least, to support ideas like social justice and supportive systems, but also extends to just presenting these ideas to try to normalise them. Representation is important, even in media that doesn't necessarily have anything to say about those being represented.
The Original Series? Given what I've seen of it, honestly, it feels quite progressive. Doctor McCoy is racist, but Spock is presented as the more sympathetic of the two, and the representation is there. The show's approach to women is... horny, but (aside from a few really awful lines) not demeaning? Like, women are objectified, but just as often they're shown to be doing just as good a job as any of the blokes, and Shatner's showing off his bod every other episode too. I (and everyone) think Uhura deserved better, but it's not like the show ever pretended to be anything besides the 'Kirk, Spock, and Dr MrCoy Adventures'; the rest of the 'main cast' were just day players that weren't swapped out before their time.
And then you have 90s Trek, where three shows shared a universe. Here, there's this thing called Starfleet, and Starfleet is definitely a military now, and it's massive now, and it appears to be the dream job for any aspiring young'un now. Chain of command is strict, decisions are made non-democratically, and promotions are apparently determined by the commanding officer. Loyalty to Starfleet and commanding officers is taken very seriously. Captains wield huge power, admirals larger still, and they very rarely seem to have this power checked. This system obviously isn't fair, since there are two very obvious cases of nepotism to be found, and that's just among the Crusher sons (and she only has two). Is that conservative? Not inherently, but a hierarchical military with intense loyalty rituals is definitely the kind of system that would appeal to conservatives, provided they can insert themselves among the new elite of the admiralty.
Starfleet's military is dressed up in enough lipstick for some Trek discussers to apply the prefix 'quasi-' to the label. Fuck that. It's a military. It puts families on its weapons-heavy flagship but it's a military. It claims to come in peace but it's a military. DS9 was very happy to show off Starfleet's capacity as a war machine when it crafted a storyline that started a galaxy-wide conflict – a conflict which from Starfleet's side was both justified and unavoidable, and which was managed by Starfleet with the kind of efficiency and capability you wouldn't expect from an organisation supposedly designed for other kinds of things. You could argue that DS9 knew what it was doing with the Dominion arc, and did the story just to bring the construct of Starfleet to its logical conclusion, but I don't buy that. Surely, if the show meant this as a critique, then the characters in the show would be used to spell that out, but they're not: no one resigns, and no one questions whether there was a way besides war to fix this. War is hell, but hell is the price to pay for heaven. Is that conservative? Not inherently, but there's nothing like a war (or the eternal droning threat of war) to increase the faith of the masses in the ruling class, and that's the ultimate goal for conservatives.
In contrast, TNG flirted with and DS9 committed to an analysis of terrorism as a tool for both good and evil. Kira's character was constructed around it, and she upholds it as the most important thing she did right up to her last episode. Michael Eddington is later lifted into a similar role, but DS9's writers' room was less convinced that he was doing 'good'. I think I can call this progressive on the grounds it shines a light on forms of protest traditionally demonised by the ruling class? It's at least much more progressive than media would be for a long while afterwards in the environment of the "war on terror".
Starfleet isn't the same as the Federation though – does the Federation do democracy? Yes, but we know very little about it. There's a president, a council, and elections just like today, but there's almost nothing else there to analyse. It might be socialist, but I can't recall any explicit confirmation of this. The Federation appears to govern Starfleet, but we only see this in action a couple of times, and Starfleet's war cabinet appears to run completely separately from any Federation government (or perhaps the DS9 production didn't want so many extras for the war room scenes). Onto this skeleton you can graft any ideology you want.
The Federation has done away with money for its citizens; all their needs are met, and non-essentials are rationed out liberally (e.g. 'transporter credits' are a thing in DS9's 'Explorers'). In short, there's UBI. UBI is an anti-conservative thing, sure, and it's presented in Trek as an idea so obviously brilliant it doesn't even need explaining. On the other hand, the post-scarcity concept was taken so far it seemed like energy itself was infinite, and energy could replace the labour of food supply, cleaning, basic construction work, and so on. To portion out infinite energy to everyone is, yeah, obvious, and perhaps a slightly different idea to the Marxist "from each according to his ability" stuff. But representation is good on its own, so "UBI is good" is still a good thing to see.
How does the Federation deal with outsiders who haven't bought in? Well, they either join, and shed most of their own systems in favour of the Federation's (DS9's 'Rapture' has a line about it), or they interact with the Federation via some kind of treaty defining the "trade". We explore this on DS9, where Federation citizens maintain 'tabs' at Quark's and hold personal stashes of foreign currency. This would all be fine, except that Ferengi society is unambiguously presented as capitalist, and we don't know how this trade with their society is defined, and it's the only one we explore in any detail. Hell, maybe the treaty demands observation of the Labour Theory of Value, but there's no explicit mention of that, and plenty of mentions of the noble ideal of maximising profit at the expense of all else; what we see in effect is the participation of Federation citizens in the exploitation of labour. Is this conservative? Not inherently, but divorcing the concepts of labour and value were so appealing to early conservatives that it became the dominant idea of the ideology, and we're still stuck in the resulting hellscape today.
The same progressive ideas from the Original Series are still present, but representation was better in the 90s than the 60s. DS9 featured a Black captain and VOY a woman captain, but there's more to it than that. 90s Trek took the bold move of widening the main casts and giving each lead stories of their own, though I note that all three shows refused to budge above 33% women in main cast (even Voyager somehow). It's a shame, then, that of the twelve women in lead roles across the three shows, only Kira, Ezri, Janeway, and Seven had a solid chunk of good stories. Also a shame that four of the eight 'women main cast slots' were recast or dropped for various reasons, versus just one dropped role among the eighteen men (surprise, it was Wil Wheaton). That could be a coincidence, but we know it isn't. The writers' rooms, production teams, and directors' lists were male-dominated throughout the complete run of all three shows. I can only assume there were a few too many men making costuming decisions too, given the bewildering outfits given to Troi and Seven (just, truly incredible that the Starfleet uniforms are right there and obviously what they should be wearing, but, no, more tits please). Is this progressive? Uh, perhaps? But it also definitely failed the women working on Star Trek, both on- and off-camera, and this context is just as important as what's on the screen.
LGBTQ representation in the 90s series is a complex one. The writers clearly wanted to try but very little made it onto the screen. Garak was gay, but only in subtext. Dax was trans, but in that "she's an alien, it's different" way. Dax got to have a gay kiss even, but that was an attempt by two characters to recapture their previous heterosexual relationship, plus they're trill so "it's different". They're all bi in the alternate universe, but they're all evil too. There was that 'gender-exploring' episode of TNG called 'The Outcast', but I feel like it stopped short of actually doing anything, and I agree with Frakes that it would've been a bit better if they'd at least cast a man in the role of Soren. In truth, 'The Outcast' is an episode where heterosexuality is persecuted, and the "therapy" to solve the problem works just fine for all we know, since the Enterprise just fucks off once it's done. So what do we have? A bunch of subtext ripe for interpretation, to be embraced by the cohost-like communities and swept under the rug by centrist audiences generally. The blank default face of a teddy bear, waiting for a toddler to either imbue it with life and expression or ignore it.
I feel pretty confident in saying Trek "did better" on race. 'Far Beyond the Stars' is especially good because it manages to be about race. It's specific and concise and difficult and beautiful, and it deploys its existing cast in ways that really give a lot of storytelling for free: fascists Dukat and Weyoun are role-playing cops, and station cop Odo is playing the "just following orders" editor. There are actually enough Black recurring cast members to fill the multiple roles required even (including the all-important Magical Negro...). I wanted the episode to go further though. It tells a story of racism by abandoning DS9's premise and going back to the past – not just their past but our past – to tell a story that a viewer could readily dismiss as being "of the past". Benny Russell was never getting to space perhaps, but now in the 90s look how well Sisko's doing. Thank God we got past that racism problem. That said, the story was still told, and it's always important to note good representation when it happens.
The 2010-onwards shows (what I've watched of them at least) have cleaned up a lot of the representation (starting Discovery with a long sequence of two women walking through a desert felt like a necessary moment given it hadn't really happened before, except perhaps Kira/Dax piloting that ship one time in DS9's 'The Siege'), but all the crap in the worldbuilding remains. I've dropped off every show except Lower Decks for the same reason I dropped Voyager: the writers' rooms are either unwilling or unable to reliably tell stories I care about.
If there's a point to all this waft, it's this: Trek is, I think, a franchise that wants to be progressive, but which has accidentally created a universe full of corruptible power structures just like those that exist today. It suggests that the wonderful progressive future is somehow going to co-exist with these structures, as though we could achieve all this tomorrow if we just, I dunno, didn't use money or something. This is what some people call "Roddenberry's vision". For a franchise less associated with progressive ideas, that's fine (creating the utopia is hard), but if any franchise were going to dive in to the details of utopia creation surely it would be this one.
After writing off anything released within the last 20 years as woke non-canon garbage, I think a conservative can probably watch most of Star Trek without feeling challenged. And that's the nub – the endless jokes about "lol did you even watch Star Trek" don't work when there's not much in Star Trek to make conservatives bounce off it. Sure, you made a woman captain, but most of the crew are men and one of those women is dressed to impress, and she's not as good as Picard. Sure, the Ferengi are worthy of ridicule, but only because they fail the vibe check – the Federation still uses their system of currency. Even 'Far Beyond the Stars', wonderful though it is, doesn't challenge the conservative viewer, because it isn't the 50s anymore, so any parallels to today are "debatable".
Pretty sure this one veered too far into cynical territory. My bad