I really do like Jenn, I think the problem is her use overuse of using a heavy foundation and a powder on top of it. It completely dried out her skin making it look terrible. If she put on BB Creams that are Korean – you can find more pale shades from my experience, and use something are for mature skin which has more moisture not because she looks old, and only use a powder under the eyes, the more glowing skin will look better and her skin won't be a dry sponge.
I think the second photo was after ter makeup was wearing off so more of her oil is coming through. The more you powder, the more oils come through due to your skin needing to make even more of it to try and rehydrate it. Her skin issues is due to her skin needing the moisture and her just piling on a tone of drying layers, along with the really unneeded shading powders, her face is already slim, she doesn't need that much makeup on her skin, and more moisturizing stuff she puts on it, the more her skin will calm down.
Glowing skin isn't "oily" looking, it looks moist and not dry. With a moist looking skin, you won't need the contour so much especially adding more "shine" back on the dry AF skin. Skip powders, your skin will thank you.