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I have both user stories.

I put Debian on the laptop of one relative, and never had to support him again (almost - he needed help setting up a printer once, which I was able to do entirely on my phone using CUPS' web interface over an SSH tunnel). I dist-upgrade him every couple of years. Totally painless. But his needs are modest - a web browser and an email client mostly keep him happy.

I have another relative who mostly uses her X220 laptop to write in Microsoft Word, and she is constantly having computer troubles. Shitty battery life (Windows keeps resetting power management to "max performance"), fans constantly blasting, endless file management issues and no backups. I am constantly having to support her, and Microsoft Windows makes that a royal pain. I knew she was going to kill that machine eventually, so I got her another X220 as a cheap backup computer, which had no OS and so I put Debian on it. I was right, her computer died, she ended up being forced to use the Debian machine, which netted her among other things triple battery life. But she was so tunnel-visioned into her particular idiosyncratic workflow (see https://xkcd.com/763/) that every minor hiccup was met with "I want to go back to Windows". It astonished me how much patience she had for Windows' daily WTFs, and yet so little patience for anything else. Within months the computer was running Windows again. I expect she'll kill that too...




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