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The power of OSS is often overstated when it comes to writing user friendly software and the sorry state of the *nix GUIs, where setting up a multi motor setup like you do in Windows 98 is still a few years away. The reality is that best practices often conflict with the need to ship resulting is wasted time refactoring, and redesigning.

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When my dad's laptop broke, he picked up my spare Ubuntu laptop and has been using it for the last two years. I know it's just one anecdote, but when it saves me a crap-ton of money and time, it seems very real to me. He could have asked me to buy Windows and Office for him... too bad for Microsoft he hasn't needed either. Game over.

What kind of things does your Dad do on that laptop? It seems to me that Linux works well for people who are very technical and people who are not. The problem is with people who want to do more than browse the web and read email but aren't technical enough to do it on Linux. For example a user who wants to record themselves playing guitar. On a mac, plug in and open Garageband. On Windows download Audacity and plug in. On Linux figure out JACK/drivers/supported IO devices. I haven't used Linux in a few years so I admit my opinion could be out of date but I've definitely noticed that the problem is for that middle group who want to do more with their computer but aren't technical enough to do it on Linux.

He's actually surprised me lately. He figured out how to install a spreadsheet app (libre office I think) and has been using it for his work spreadsheets (he's a contractor).

To be fair, he probably wouldn't have been able to set it up initially by himself. But I've had really good luck getting family members on Linux lately. I can Ssh in and do updates or make changes and it's way easier than remotely administering windows.

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