• Custom DNS servers specified on the device to circumvent the pihole
• dns over https or tls
• hotspot from approved device
• alternative YouTube front ends

These are just off the top of my head. Best case scenario the blocking does work and the teen never tries to bypass it. They’ll still just move onto “wasting” time on something else. This is treating the symptom and not the root cause.

Pihole can set up “groups” for different blocklists. You specify client by IP or MAC address so it doesnt matter what the dhcp server is, so long as there’s a static IP or static MAC address. My pihole server doesn’t have dhcp set up and I’m able to do this fine

Though from personal experience this just becomes a game of cat and mouse, and if you have a motivated teenager then they will find a way to circumvent this. For example android can rotate MAC addresses, and IP addresses are trivial to spoof as well.

Haven’t used all of those but my recommendation would be to just start trying them. Start small, get a feel for it and expand usage or try a different backup solution. You should be able to do automatic backups for any of them either directly or setting up your own timer/cron jobs (which is how i do it with rsync).

I submitted a response but if i may give some feedback, the second portion brings up:

I am willing to pay a substantial amount for hardware required for self-hosting.

This seemed out of place because there were no other value related questions (iirc). Such as:

• I believe self hosting saves me money in the short term
• i believe self hosting saves me money in the long run

I’m sure you could also think of more. But i think it’s pretty important because between cloud service providers and any non-free apps you want to use, it can be quite costly compared to the cost of some hardware and time it takes to set things up.

The rest of my responses don’t change but if you’re wanting to understand the impact of money in all of this, i think some more questions are needed

Best of luck!