I collect old computing equipment and I have a number of machines that run old software. The biggest problem with old operating systems (mostly Windows, but others too) is that modern web is unusable without TLS3 and back porting that to old browsers is pretty much impossible...
How many times "I just wanted to download one file" on a windows 98 machine. The only "solution" is to maintain a proxy running a modern OS that renders modern web as image maps.
As for Word 97,I remember when it was new. I also remember when Microsoft went to the "new" ribbon interface (it was much later, 2016 perhaps?) I hated it, my users hated it... Fast forward a decade and last time I tried to use pre-ribbon office product It was extremely inconvenient to use. I don't know if it is due to high dpi screens or something else. This and lack of good dictionaries is the main reason why I continue to pay for MS office instead of using Libre office (or one of ancient office products I own) for example.
Half the browsers I use are still compatible with HN despite being 10+ years old. The other half I mostly use on my own websites, which allow plain HTTP.
How many times "I just wanted to download one file" on a windows 98 machine. The only "solution" is to maintain a proxy running a modern OS that renders modern web as image maps.
As for Word 97,I remember when it was new. I also remember when Microsoft went to the "new" ribbon interface (it was much later, 2016 perhaps?) I hated it, my users hated it... Fast forward a decade and last time I tried to use pre-ribbon office product It was extremely inconvenient to use. I don't know if it is due to high dpi screens or something else. This and lack of good dictionaries is the main reason why I continue to pay for MS office instead of using Libre office (or one of ancient office products I own) for example.