I'm not young either and my favorite senior is mom. I've been using the following recipe with reasonable success for a while:
- Setup a bridged (site-to-site) VPN tunnel on the device, so that the "maintainer" can fix almost anything on the remote network and have screen sharing work ok. Things will go wrong, that's one thing you can be certain of. Human interaction will be necessary.
- Have a "lab" for test and integration before deploying anything new. A must if there is no site-to-site link
- Use some system monitoring and watchdog to help ensure consistent behaviour on end-user devices
- Color-code every cable and plugs on the device, block unmanaged ports. Yes, once mom was plugging the PSU into the HDMI port on the Pi. Try it, you'll see it fits, sort of.
- Tuck an extra SD in the Pi as cold spare for disaster recovery, or setup USB boot from a rescue key.
Cloud services are fine, but they lack consistency due to the "continuous improvement" thing. I prefer to proxy services as much as possible.
The iPad is giving me a hard time as it is on the network but not remotely accessible as a Desktop would be. Adding a camera to the site would sometimes help troubleshoot issues. I work around it by having the same system to test on, but it is not ideal.
"S'il n'y a pas de solution, c'est qu'il n'y a pas de problème." Les Shadoks, J. Rouxel