I have a tech illiterate mother in law who I switched to Zorin OS (an Ubuntu fork).
I installed a wireguard VPN client on her laptop and did drills over the course of 3 days to make sure that she understood how to connect. Anytime she needs help, I can tunnel through my wireguard server and log on with my own account - Heck, as long as she doesn't change her password, I can log on as her as well.
That has made remote troubleshooting significantly easier as she is located about a a 23-hour drive away.
There's nothing worse than taking extreme measures to troubleshoot a problem with a third party system that's out of your control.