I didn't read your choices but if you really want to help you family out, you make your brother earn his car. If he wants to drive your car then you make him pay for it. You can call it a rental fee. You also make him pay for his own insurance. Honestly, paying for him will not teach him anything and he will not appreciate anything he has as much as him earning it himself. This is something I learned from my mother and I will forever be thankful for it.
If you make him pay for his own things then he will have a life long lesson that will forever help him.
In the end, what you can do is save the money he pays you and give it to him as a birthday gift later on or graduation gift. Whatever you want to call it.
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