his family has money

Major red flag then - if he's not even spending money on you he earned himself, then he's just seeing if he can buy affection. He sees this as a transactional situation, and he will get nasty the moment he feels he won't get the returns on his "investment".

Btw. as others have pointed out, I also agree that it is already a red flag even if it's his own money (paying for time/activities spent together on a first date gets a pass from me, but paying for things you buy for yourself does not). And the comment about the transactional nature also applies there.

Way to tell if someone cares about you: they ask meaningful questions about you, your life, your thoughts, your personality. Red flags: they focus on doing things that you pay for, and they mostly talk about themselves or job/money.