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.
