alt Hacker NewsWe made the call to go Apple years and years ago when he was always fighting viruses and virus scanners on Windows. His Macbook was still (hardware-wise) perfectly functional, but does not receive security updates anymore, so he went iPad. Indeed there are more problems than expected. I expected even less IT support from me was needed. Instead he now complains about the lack of control (which I am certainly ok with btw, the complaining I mean.)
The current plan is to put Ubuntu on the Macbook, not sure what to do with the iPad but make it less "primary computer" will be one of the policies to implement indeed. Maybe he will be happy with an external disk and f-spot, and his music nicely sorted into files. Then some generic backup solution to a Synology NAS or something...
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Have you considered open core legacy? I am running macOS Sonoma nearly perfectly on a 2010 iMac.
Macbooks are great devices, but Linux is a great "fire-and-forget" OS for situations tech-illiterate loved ones. I've done it many times, with much succes and satisfaction (on both ends) without barely any aftercare. All you really need to do is teach them to install those updates and install a major upgrade every few years (or not, Ubuntu will run fine for a decade).
This is why I direct most family to Apple devices. Otherwise it’s constant tech support.