Lately I've been strongly considering helping migrate my parents to Linux. Their needs are primarily web-based with some basic productivity tools mixed in, and Windows has just been getting more and more hostile. On top of this, they're at an age where they're now more susceptible than ever to various scams/attacks, and shutting down an entire category of problems by removing Windows from the picture is increasingly attractive.
I had forgotten that Chicago95 exists, but this might be exactly the right thing. They'd immediately find it familiar, and while the theme isn't the whole story, this would go a long way in easing the transition I think.
I miss this era of computing.
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