To be fair, early wine (when I first tried it) wasn't very usable, and for gaming specifically. So if you were an early enthusiast adopter, you might've just experienced their growing pains.

Also, I assume some Windows version jumps didn't make things easy for Wine either lol

The hype/performance mismatch was significant in the 2000s for Wine. I’m not sure if there was any actual use case aside from running obscure business software.

Yes, there was “the list” but there was no context and it was hard to replicate settings.

I think everyone tried running a contemporary version of Office and Photoshop, saw the installer spit out cryptic messages and just gave up. Enough time has passed with enough work done, and Wine now supports/getting to support the software we wanted all along.

Also, does anyone remember the rumours that OS X was going to run Windows applications?

It took some futzing. The crusty PlayOnLinux UI is permanently etched into my brain.