There’s some guides for the “best” TOS episodes. Go find one of those and cherry pick in order.
Then restart TNG. The way Wesley is treated is character development for everybody.
All of DS9
All of Voyager
Then the newer stuff. I’d leave SNW for last since it’s still releasing episodes. Lower Decks you can do whenever, I feel like it’s easier to pick up and watch than the others.
A lot of LD won’t land as much if you don’t really know all the references. I guess it’ll be the opposite of what most of us experience which is the original content and then the references, it’ll still be fun to have all the references show up in LD and then uncover them in live action.
I wouldn’t assume that it works best in that direction even though that’s great for long time fans like us.
There is an entire new cohort of younger fans for whom Lower Decks was their entry point. It’s successful because you don’t need to get all the Easter eggs and references to still find it an enjoyable show.
In fact, I see a lot of those Lower Decks-first fans talking about how the show gave them enough reference points to really enjoy the classic shows and be open to their slower pacing.
You can still enjoy LD on its own, you just won’t pick up on all the Easter eggs. SNW and LD are modern shows and what a modern audience more of what they expect these days (DIS too, but it being heavily serialized may be AA turn off to more causla viewers). TOS can be very campy at times, a product of it’s times, which makes it hard for some.
I guess what I’m getting at, is that it’s OK to enjoy the new stuff without knowing the 50+ years of backstory.