Everyone is different, but I generally use https://kethinov.com/startrekepisodes.php to guide my viewing experience.

Anything that is a 7 or better on the audience scale, I watch. Anything less than, but has a high personal score from the maintainer I generally give consideration.

It includes a lot of trivia and additional details that may help me get some of the cultural references I could otherwise miss. The episodic nature of the early shows mean you don’t miss much skipping around. If you finish a series and want more, go back and watch everything above a 6 and so forth.