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It's at least partly cultural. We'll pay for hosting, or internet access. Why won't we pay for other services if they're valuable to us?1. Too many separate subscriptions become hard to manage. Example: the banks in my country don't allow direct access of my account movements to any budgeting apps so I have to tally everything manually because I want to track my expenses. There is a business idea here somewhere: a subscription aggregator or some such, where you can manage a total subscription budget per month and be able to cut a service easily (which is of course strongly against the interests of those you subscribed to).
2. Cynicism. I have physically met and conversed with people working in ad-tech. They have zero scruples. If you pay for a service these people will laugh at you, collect your money and then proceed to inject trackers and huge banners in the website/app with no regard that you paid for the service. You don't magically disappear from tracking once you pay. That's sadly a myth. Your narrative is correct on its surface but it was perverted and abused.
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I agree that the free tier services is like running a charity and not everyone feels like they have to. There is a business opportunity for a better model of free trials and NOT to automatically subscribe you after a week or a month. Whether that new model is in the financial interest of the gatekeepers (Apple / Google and the apps in their stores) is another discussion entirely, though.
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Finally, I am OK paying a few more bucks a month to my ISP. So let all those services figure out a way to charge the ISPs. I'll gladly pay anywhere from $5 to $50 extra a month for everything that I consumed that is viewed as non-free.