I bought them Chrome OS devices and I haven't had to do any tech support since. Phone wise, I have them on Android and I haven't had many problems, but I should have moved them to iOS when they were younger, as I find iOS UI is more stable across upgrades, which tend to leave the phone more or less behave how they used to and new behaviours are usually behind new settings/buttons. And elders who are not used to technology usually struggle whenever there are any UI changes.
Not only older people. Already since the beginning of computers there have been changes just for changes sake in everything. My theory at that time was that the changes were done so they could sell new education courses for companies every time they upgraded the software.
Now sometimes I have to google how to do things that should be very simple even in Windows or Android but now the setting is hidden to not confuse people...