There is certainly something intangibly attractive on this era and style of software. On top of my head I'm thinking fb2k, mpc (and its forks), virtualdub, utorrent (the original 1.x series), irfanview, kerio firewall (classic 2.x series), putty, even maybe mirc and notepad++ to some degree. Small programs, classic Windows style controls, emphasis on staying out of your way, somewhat minimalistic and barebones but still remarkably powerful and capable. These to me represent the golden age of Windows.
Of all these programs (and there were many), fb2k is the one that I still use on regular basis while almost all the others have faded away.
Seeing this from the outside, I can't shake the idea that Microsoft's complete fumbling of offerings for UI development is to blame. There are so many new paradigms in user interface on Windows that led nowhere, are completely inadequate for modern development, and yet are still supported by Microsoft. The company has lost the plot, and we're left with Microsoft even devolving into web apps for the desktop, with the success story of VS Code leading the charge.
If Microsoft could find one good path forward for UI development on Windows, we'd want those small boutique apps to get with the times.
I feel like (with no research) these interfaces were designed by programmers first and foremost and have a tight coupling to the actual underlying code.
A "well designed" interface with "good" UI/UX from a proper designer may have best practices, but additional layers of abstraction from the functionality which makes everything feel less direct.
I think (with no research) that people were more respectful of HCI guides. And even skeuomorphic is hard to do well, itβs more grounded in terms of UX. Buttons were actually buttons and icons were more understandable. Now, design is an abstract art challenge.
Of all these programs (and there were many), fb2k is the one that I still use on regular basis while almost all the others have faded away.