Just found an «evil» little #chocolatey package, that is even excluded from moderation. Basically it just makes it easy to create two Scheduled Tasks to run «choco upgrade all -y» – and kill it a while later in case it hangs.
choco install choco-upgrade-all-at --params "'/WEEKLY:yes /DAY:SUN /TIME:20:00 /ABORTTIME:22:00'"If you prepare a PC for a family member and just want it to be a no-brainer that automatically, that’s quite handy. Pay attention to the order and number of quotation marks and apostrophes!
More information available on the package’s page.