Why not just go through it in order? Make the new stuff a treat earned for getting through everything else. I'd start with the TOS pilot and go forward. She'll either like trek or she won't, jumbling it up isn't going to make her like it more, but it may make her like it less.
The cool thing about star trek is I can pretend I knew that and am speaking from the perspective of Discovery in the 29th century or something and still be technically correct, the best kind of correct.
In the United States, millions and millions of people walk around with conditions we can treat with our own kind of magic: modern medicine. So why don't they get that prosthetic arm, treat that chronic pain, get that surgery, or take those pills? They can't afford it. Why don't they get that vaccine? They don't believe in it. If magic exists to eliminate all disabilities, then there should be no smart, rich people with disabilities in your world building, certainly. Plenty to go around otherwise though.
The unspoken part of that argument being they deep down desire a world that has no non-white, disabled, queer people in it at all and don't understand others don't think that way.
Any single word in quotation marks. Reread sentences with any single word in quotes as if some conservative know-it-all is rolling their eyes and scoffing at these quoted terms. Putting them in quotes quarantines them from having to be taken seriously and is setting them up for criticism. If they didn't use quotes for terms they didn't like, they might be accused of being complicit in the "woke mind virus" that has stupid people so terrified.