Perhaps gently ease your way into it, with the movies first. In reverse order. Then, less culture shock when jumping to TOS.

A lot "hero gets the gal" [or doesn't] crap shoe-horned in to (afaicr) every episode. Gets me wondering what trek could be, freed from the producers, the corporation, the industry, etc., not just how different standards from then to now, but what flawed standards of our times could be more savagely exposed. If they were making those mistakes then that we see now, what mistakes are we making now (or even 30 years ago), that are yet to be exposed (by just socially evolving past).