Am I overthinking this, or are these red flags?

I'm 23F and he is 24M. I’ve been talking to this guy for a while, but we’ve only been going on dates for about a few weeks now and aren’t officially dating.

At first he was very generous—dinners, drinks, gifts, telling me I “don’t have to worry about money". I never asked for any of this, and I’m not expecting a guy to financially provide for me. I naturally reciprocate with little things like coffee, treats, and gifts.

But he’s also made a lot of comments about money. He says he believes relationships should be 50/50, men shouldn’t automatically be expected to be "providers", and he wants to be a stay-at-home dad someday (wants a family really bad and is super oriented on doing that asap yet doesn't want the responsibility??). He’s talked about being “traumatized” by exes because they had expectations for how they should be treated and how felt used (like being taken out to dinner). Even complimented how I was "low maintenance" because I don't get my nails done or don't mind buying treats here and there which is a green flag (not sure how to feel about that..). He told me that if he gives me “princess treatment,” he expects “prince treatment”—for example, if he buys drinks for my girlfriends, I should buy drinks for his guy friends. All because he is a "feminist"...He’s also mentioned a lot about me buying him gaming consoles, taking him on trips, and keeps mentioning that he likes gifts. Saying that he doesn't want to work either even though he has a nice job that pays really well...

Not much of that alone necessarily bothered me, but it made me wonder if his generosity comes with expectations.

Immediately after one of these money/50-50 conversations, he came to my apartment. I told him where he needed to park, but he chose not to because he didn’t want the inconvenience. His car got towed.

I panicked and offered to help pay because I hate financial situations becoming awkward and my instinct is to over-adapt and make the problem go away. I didn’t actually feel like I owed him half.

The next morning, he reassured me that I shouldn’t feel bad/guilty, that it happened at my place, and that he’d park in the right spot next time. So I thought that was the end of it.

The next day I went on a little trip with my friends and was barely on my phone. I was overwhelmed and somewhat withdrawn. He noticed and asked if I was upset and seemed worried I was pulling away. I told him I was just busy. A few days later, he randomly sent me a Venmo request for half the towing bill. The timing really bothered me. It honestly felt like he asked because he sensed me pulling away, almost out of spite, although obviously I can’t know his intention. It felt especially weird because he had already reassured me that I shouldn’t feel guilty....

He also knows that my family has a history of financially invoicing/charging me for everything. I’ve told him about this, and he’s specifically said that what they do is fucked up. So having him come back days later with a money request felt particularly shitty.

I told him the request made me uncomfortable and explained all of this and all he said was is that we should drop it and forget about it??

I'm not sure if I'm overreacting thinking this is odd/red flaggy?!