Relative to the time in which each was released Trek has gotten less progressive over time. TOS was released during the height of the cold war and the civil rights movement. It had a black female bridge officer. The line of command isn't super clear on tos but Uhura was a department head and no lower than sixth in command. It had the first interracial kiss on television between Kirk and Uhura. It had a Russian bridge officer, also no lower than sixth in command. It had an Asian bridge officer also no lower than sixth in command. Earth was presented as a Socialist utopia.

TNG didn't really back off of that ideologically, though it didn't do as good of a job with racial representation, but it also didn't advance it and culture did advance between the 60s and the 90s.

DS9 pulled back on it primarily as a result of its exploration of darker themes. It creates and drives wedges into cracks in Earth's Utopia. It has Starfleet and even the main protagonist abandon Starfleet's ideas and principles in periods of adversity. It also started the movement away from the philosophical sci-fi that Trek thrived in before to more action oriented sci-fi.

Ultimately, imo, Janeway was a more "Starfleet" officer than Sisko. She showed more integrity and dedication to the Federation's ideals under greater levels of hardship and personal risk. All in all Voy was not particularly more or less progressive than DS9 though.

Nutrek tries but it's too action oriented and doesn't really explore the themes in a meaningful way and that causes its more progressive moments to come off as less impactful and less integrated into the story. It also seems to forget that Starfleet is a quasi military organization and doesn't always do a good job at presenting the characters as competent disciplined professionals which makes progressive decisions and moments less meaningful.

So, I agree. Trek isn't woke enough. It should bring Roddenberry's philosophical progressive Trek into the modern era.