Yeah, that's definitely one solution. But how many normal people are going to do something that complicated? 0.

Ultimately, you still have to be running a VPN. Otherwise your ISP can see the requests going to your Bostr on the VPS. Ultimate truth is that there is only so much you can do to lead a horse to water.

We should all strive to run software and services and businesses that respect user privacy as much as possible and track as little identifying data on them as possible. The real trick would be figuring out how to structure the incentives for businesses such that they really don't want your private info. E.g. it makes their businesses easier or more profitable without it...