Do u think Harold was stupid for reaching for his gun?

I don't think he was stupid for reaching for his gun. If I remember correctly before reaching his gun he was talking to Caine saying to run because he said "I , ain't goin down like a bitch." So I think he knew he was gonna die at that point by either the guy with the hand gun or the guy with the shot gun so he was gonna go down a blazin. But that didn't turn out as well as he planned. Was a good plan though but totally backfired.

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I had the impression that all he needed to do was quickly get out of the car?

Yeah, if a squad of people has guns pointed at you, you run no matter what. There's a difference between defending yourself and being stupid.

Wendy? Darling? Light, of my life!

In reality those dudes was gonna kill him regardless, so he knew he had to shot first. What I dont understand is why they didnt kill Caine, they shot him but they didnt make sure he died.

Every character in this film was stupid, aside from the teacher.

Foolish for sure, but Harold probably knew it was curtains for him whether he got out of the car or not and just wanted to "go out like a G"