Windows 98 holds up better in modern terms, and there you had things like USB support build right in.
I remember being quite disappointed when the toolbar buttons went all flat, as I felt that was offering a consistent UI (button -> 3D look) on the altar of design. But I think that came with one of the Office versions first. (QA was horrible back then, if you had a Windows applications, you had to cross-check it with every ofice/OS permutation, as both wreaked havoc on your UI dlls).
I used to love hacking about with the Win32 Apis in the old days. I wrote all sorts of neat tricks like turning the start button into a paddle for a weird desktop-based game of Breakout.
I've done a bit of fun "repurposing" of the Win32 controls too, and that is something I'd definitely love to see --- probably along with quite a few others on HN.
https://www.planet-source-code.com/vb/default.asp?lngWId=1
I was an obsessive VB6er.
I still have an unclaimed prize ticket for winning best submission one month.
It's a pity the owner never gave the UI more love as that site had the member base long before StackExchange et al but it just failed to compete. Even now, it still looks like a 90s site and that's not even the same design it had in the 90s.
The game wasn't pretty though. But it was thrown together when I was at college and should have been writing course work. In fact, I'd be surprised if it would even still play on modern Windows.