Such a hard agree. My wife won't even let me install Linux, which takes out the more technical aspects of the above.

She's just comfortable on Windows. Most people don't want to learn something new and even fewer actually care about privacy.

Edit: Us Linux users assume that if Windows gets bad enough people will switch to Linux, when we all should face facts that normies will much sooner switch to Mac.

Mostly yes but there's one other option that simplifies the whole thing: Chromebooks. They're actually pretty decent for someone who doesn't need much beyond a browser, a mail client, and a basic office suite.

Sure, they're tied to Google with all that entails but they can be a real option for someone like a senior who relies on relatives for tech support.

Something I've never checked for but...are there any linux installers that run from within windows? Shrink the windows partition, create a linux partition, populate it, install grub, and tell the user to reboot and choose linux? I think general lack of good ext4 fs support in windows might make things difficult, but you don't actually need to do that part from within windows. There could be a second installer that's triggered the first time they boot from grub.

I feel like a well supported installer like that would dramatically lower the barrier to entry. It could make dual booting windows a breeze for anyone who knows how to run an installer and reboot, which is what people actually want.