My wife recently started to show an interest in watching Star Trek. Previously she had seen The Wrath of Khan when she was single digits in age and not much else.
So far we have watched some of the first season of TOS and some other key episodes (still need to show her Mirror Mirror and The Trouble with Tribbles for sure, and probably episodes with Pike, which I think is starting to come up for us soon).
We watched a few episodes of TNG, for some reason Paramount through Amazon started us in the middle of season 3 instead of the season 1. She did not like how Wesley is treated on the show (she is a huge fan of Wil).
From there we moved to Voyager and are about half way through the second season. She is liking it, but not a fan of Neelix (I cannot wait to tell her he improves after Kes is gone) because of his jealousy towards anything that interacts with Kes. I have never finished watching all of Voyager myself, I think I am in season 6 or 7.
I watched all of Discovery (I think I finished anyway), the first Season of Picard, most of Strange New Worlds, and some of Lower Decks. Since she has said she wants to watch the new stuff with me I am doing my best to not watch it all so I have some new episodes with her.
At what point would you move from the old stuff to the new stuff to keep someone from being too confused? Or if confusion arises would you go back and watch the old stuff to answer questions? I know we will not watch Picard until we have gotten well into the Borg stuff in Voyager and some episodes of TNG dealing with it.
I’d recommend release order because there are callbacks and crossovers, cameos, etc. that tie these shows together. You could watch the in any order, but you’d get more enjoyment out of picking up all the references and easter eggs. So, TOS -> (maybe TAS) -> movies 1 through 6 -> TNG -> movie 7 -> DS9 -> VOY -> movies 8 through 10 -> ENT. Then modern stuff like DSC, SNW, PIC, Prodigy, and LD.
That said, there’s no need to watch every single episode of every show. Back on Reddit there were guides of “essential” episodes for each season of every series. Here’s one for TNG. I’m sure you could find this for other shows too.
Bonus point for watching episodes in release order when therewere two series running at once.