Windows 2000 would be as far back as I would reasonably go to still be comfortable enough for "daily driving". But we'd need an unofficial patch that backports

Windows 2000 would be as far back as I would reasonably go to still be comfortable enough for "daily driving". But we'd need an unofficial patch that backports all the security holes and updates the root certificates, so that modern browsers can be (securely) used. If you're talking about gaming only, my dad still has a working 386 running DOS and Windows 3.11 with a few games from 30 years ago. The clickity-claky noises made by the spinning disk and floppy bring me warm nostalgic feelings and I enjoy 20 - 30 minutes of Prince of Persia or Wolfenstein 3d when I get to visit, but it quickly looses its appeal and I would most definitely not want to be using it as a "daily driver".