[zfa]

I mean if it floats his boat then why not.

But it looks like a lot (all?) of the work here was just to get pi-hole functioning well - and that now needs him to deploy pi-hole, cloudflared, caddy plus all the surrounding tools of Docker, Docker Compose, Ansible etc.

You're spot on that if he'd have applied some thought outside of simply 'fixing pihole' he might have seen there are more modern and elegant solutions to configure network-wide adblocking.

e.g. AdGuard Home is an opensource single-binary precompiled for most architectures and OSes. Self-updating with an HTTPS multi-user GUI; supports DoH, DoT, dnscrypt out-of-the-box. Has a single yml config file to backup/sync; supports adblock lists based on regex as well as hosts file format.

Downloading and running that one little binary gives him the endgame he wants a lot more elegantly.