Is apprehension the red flag to leave??

I have a bf for several years who you really loves me and wants to marry me. I’m really hesitating moving forward because of what I see as a possible red flag. In particular, he has trouble with making the right financial decisions sometimes. He doesn’t spend money like a drunken sailor but he underestimates financial effects. Examples are: he in the past has way overspent on credit cards and but for the Gift (see below) he only made modest payments; he doesn’t think you need much money to retire (he is retirement age) if you collect social security and work (and with about $25k in the Bank that was a gift to him which he refers to as a “windfall”); he on occasion uses a credit card for himself that account belongs to his elderly parent but he is authorized to use it (even though he has his own credit cards and money to pay it); he is the power of attorney for his parent and hasn’t paid off his elderly parent’s credit card because he says if they die the balance will be forgiven even though the parent has enough money to pay almost all of it now; he wants to give me his paycheck once we live together and I can make the financial decisions about how to spend the money. He says I shouldn’t worry about his financial decisions since I’m good at making those decisions and we will “balance each other out”. If we live together he will live in my beautiful home (he has an apt) etc.; other than what I’ve mentioned he has no assets except a car with a loan. Am I blowing this out of proportion or do you also see a red flag enough for me to leave him even though I really love him too??? Is it unrealistic to expect someone to be financially independent and prudent too?