I really liked the podcast, from the perspective of someone who has a healthy net worth and is dating someone with a lot of student debt. I thought it was really sweet how the boyfriend was good at optimizing without loading it up with emotion - the math just made sense for him to contribute to her debt if they were going to be building a life together. It does seem like something that's really tough to do without creating resentment or feelings of obligation, and I'm rooting for them.
Put me in the camp of finding it not ok to criticize (or even comment on, really) how a woman of color handles her hair. The topic is just WAY too racially and politically loaded for me as a white woman to have any opinion on. Plus, neither of them seem interested in FIRE, so if they keep working in their MBA jobs for the indefinite future, this is a totally manageable expense. Plenty of us here spend similar amounts on things that other people don't get, and we just work it out in other parts of our spending (see e.g. the housecleaners thread, cross fit, kids, pets, travel, whatever).