alt Hacker NewsI beg to differ, I tried that approach a few years back with my folks, only to discover on my next visit a few months later that they went down to a local PC store and got Windows re-installed.
They never managed to get it working for their liking, it wasn't able to run the stuff their friends used to talk about or share via CD/DVD/USB sticks, and they did not wanted to bother me with "dumb" questions.
So I rather that they have Windows, go down to the local PC store when something isn't working as it should.
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Of course you need to help them to alternatives, if they are not that tech-illiterate that they have very specific wishes for software.
It's been a while since I experienced people sharing software one discs by the way, it's been a while since I saw discs at all ;)
I do the same with acquaintances whom I sometimes sell secondhand gear, I don't want to do any support so they get Windows. For my father it's different, I can do support, plus he really appreciates and is willing to make sacrifices for, the privacy angle.