I don't have even the smallest idea how to configure one or what software I actually need, BUT, my greatest fear is that I'll end up with a pretty "broken internet" since I won't be using a residential IP anymore.
Cloudflare will just think that I broke into some random wordpress site and started using the server to ddos (who? with 1-2 requests/minute?).
It doesn't look that they implement any kind of serious IP reputation algorithm. I have a static residential address since I remember signing the contract, almost a decade ago, pretty paranoid about security with a clean PC and I never seem to stop getting captchas.
Is PIA a paid only service? I doubt any "hackers" will be using it to break cloudflare sites. On the contrary, I'd argue its users are actually more civilized than the residential folks.