Yeah I think that would be an OK case and these specific things can be up to the moderators of communities. I know that some communities require mod approval before self promotion is allowed, so I think in the CGP Grey community case it would be a non issue.
I think starting with a super specific rule around affiliate disclosure as proposed would be good enough to avoid this particular problem.
Yeah I saw a post about it a long time ago on Reddit for users with lots of devices
Basically it is just setting up one or two "central devices" that know all the client devices, but not linking the client devices individually.
IE: One server is connected to your phone, laptop, tablet, desktop, etc. But the phone is not directly connected to your laptop or desktop or tablet.
To be fair I don't actually know if this is the best approach anymore or if just connecting all of them in a mesh is better 🤷
Here is a forum post describing it.