I recently read a review of 1990s pop aesthetics, and it was probably intentional for reasons that resonate with us again. In the 90s, with the advent of omnipresent computers, organic, amateurish handwriting became really popular, and I think that’s what comic sans is good at looking like.
Haa been for decades iirc. Windows is free, but customization features are locked behind a license. I remember my dad’s Windows XP being unlicensed, and the biggest issue was just a notification in the bottom corner.