[quote=@GreenGrenade]
I dunno, I don’t think they’re dated if they work. Spider-Man (Peter, specifically) has probably the best supporting cast in comics, and I think the MCU kinda fudged themselves by trying to shove them aside and give us new, much lesser alternatives.
[/quote]

A good deal about what made Spider-Man such a hit was how relatable he was. Stan Lee said he created Peter Parker because he wanted a character for his young reader-base to identify with.

Obviously, Spidey is such a well written character with such a colorful supporting cast and rogues gallery that relatability isn't necessary to make his movies engaging and interesting. But him being a teenager is the core appeal. And modern day teenagers (most of them) don't live in a world with Raimi or even Webb's versions of Flash Thompson. They're caricatures of the often violent and insane bullies we saw in older films in the eighties and early nineties. It's hard to pull that off and expect a modern, young audience to be pulled in like your older viewers would be.

I'm not saying the reboot was necessarily successful- but the idea behind it isn't wholly without merit.