Should I file FAFSA before applying / even if I don't know where I'm applying yet?

Your brother will be an independent student and will be able to fund himself. If he is applying for a PhD program and is not getting full funding, then he should not be attending. Your brother will be able to take out a grad plus loan for his masters leaving your dad with the resources to assist you in your undergrad education.

if dad is not repaying the loan, it will be considered income and dad will have to pay tax on the loan.