One of the big problems with the 2 tier system you describe, is the most valuable users to advertisers are the ones with the type of money to pay for a subscription to not see ads. So by having an ad free version, you are devaluing your platform to advertisers. I’m not saying the 2 tier system can’t work, it does for plenty of things, but it is why a lot of websites don’t offer it, or avoid it for as long as possible.
Yeah, this sounds like the whole “green bubble” thing that I heard about. Where kids were seen as poor if they had a green bubble in iOS, because that signified you weren’t on an iPhone. That was way after my time in high school, but if it had been a problem when I was there, I know I would have not wanted to associate with any kids being that judgy.