I’m about to get a $1500 hospital bill which is after the insurance contribution. My new insurance is awful. How do I go about facing this?

I heard about the itemized list, and I also see they have financial assistance which I would qualify for being under 400% poverty level. The question is, when this bill arrives, in what order do I proceed? Do I ask the hospital for the itemized list before applying for the financial assistance? Or apply for the financial assistance first? Or does it not matter? Anyone have similar stories and how you handled it? Thank you everyone.