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TOS season 1. Unusually for Star Trek, TOS came out swinging but soon lost its steam. Seasons 2 and 3 are pretty forgettable with the exceptions of the few that make fan-favourite lists. Season 1 is generally good and occasionally brilliant. TOS top ten lists are season 1 heavy. Also, skip anything written by Gene Roddenberry himself. Fantastic producer, dreadful writer. He really was Star Trek's George Lucas in many ways.

And now for TNG...

TNG has two eras. Seasons 1 and 2, and the rest. The former was made up largely of recycled scripts Roddenberry wanted to use in his never-made "Star Trek Phase Two" planned series. There's a reason that so many season 1 and 2 episodes seem like the away teams are just find-and-replace'd Kirk/Spock/McCoy, because they often were. As a result the characters never really get a chance to be their own characters. He liked to fire, or encourage to quit, those who disagreed with his creative decisions.

Between seasons 2 and 3, Roddenberry's health was too poor for him to micromanage the writing room with dumb ideas. The writers then unleashed the actually-good scripts they'd been writing and polishing on the side without Roddenberry's knowledge. It was effectively a brand new series. Writing drastically improved, the actors got to actually emote, the visuals and sets were far more polished, it was a glorious fresh start. It's funny to go back to watching season 1 or 2 episodes after seeing 3-7, it's like you're watching fan films.

Skip episodes not specified, they generally range from bad to worse.

Season 1: Encounter at Farpoint (not great, but it is the pilot episode, so ya gotta get through it), Where No One Has Gone Before, Datalore, Home Soil, Heart of Glory (a genuinely great one), and all the episodes that come after Heart of Glory. They're usually good and also necessary to understand some characters motivations later.

Season 2: Elementary Dear Data, The Measure Of A Man, The Royale (very dumb but also actually pretty funny), Time Squared, Q Who (do not skip this one, this sets up so much), The Emissary. People say that season 1 was the worst, but they are wrong, season 2 was a trainwreck.

Season 3: Everything. My favourite out of that season of absolute bangers is "The Survivors" which I will not say any more more about, I would never deprive anyone of seeing this for the first time.

Season 4 is on par with 3 in my opinion. The following seasons are what I would call "good to great" and not "great to amazing" like 3 and 4. Still well worth seeing though!

And now for DS9!

Don't bother until you've seen at least up to and including TNG season 4's first episode. DS9's pilot doesn't just spoil the end of TNG season 3, it makes no sense without it. You'll have no idea what's happening and why from second 1.

Personally I think DS9 started strong and lost steam gradually. Most of my favourite episodes like "Duet" are early on. I liked the original premise of the Federation lending a hand to an allied world to help them rebuild after a long and brutal occupation by a colonizer. I'm not a fan of a later long-term war arc that changed the tone of the show. And "In The Pale Moonlight" is so fucking overrated.

Let's talk Voyager, Discovery, Picard, and Strange New Worlds!

Voyager was the best among them. And even then I wouldn't recommend it unless you're like stuck at an Antarctic research station and you're desperate for something to watch that you haven't seen before and you have unlimited free time. I'd bet that there's better uses of your time in your current situation though.

Let's now talk "Star Trek Enterprise"!

Wow, what a missed opportunity this show is. I'd suggest skipping it until/unless you get done with the better shows and want some prequel-type stuff. And even then I'd just skip right to season 4, and don't watch the finale. There's genuinely good stuff early on in season 4. And basically nothing that happened prior to season 4 actually matters, there's a lot of dumb in 1-3.

And now for the modern crown jewel, the glorious rise to the triumphant occasion that is the act 3 in the TNG/DS9/LD arc...

Lower. Fucking. Decks.

You will need to see the entirety of TNG (and at least read a wikipedia entry about the Dominion War from DS9) to really get some of the emotional moments from this masterpiece of a show. 5 seasons, 10 episodes each. 50 episodes is all we got. And every last one is good. The long arc isn't about some grandiose plan to destroy the galaxy or some bullshit. It's a deeply personal story about a troubled young officer who's suffering from war-related PTSD and other personal pressures. She is not coping with it well at all.

But she is a lot of fun to watch as she heals.