I would have it run until Kirk takes over as captain. Then jump forward to just after The Motion Picture.
This not only gives them about a decade of time before TWOK that’s barely been touched by the screen canon, they can do a design revamp to freshen the series up using TMP as a starting point, and they handle the fact that with a series per year the actors are going to quickly age ahead of their characters.
I think 'The Devil in the Dark' from the Original Series would be a good option. As would "Lift Us Where Suffering Cannot Reach" from Strange New Worlds.