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Windows 2000 Professional was peak Windows for me. Skipped XP etc thanks to mac. Then 7 for a while.

This is the correct answer. Win2k was probably the most solid and cruft-free release that they did.

Then the enshittification started with Window XP, jelly-mold/curved glass buttons, activation, and .NET everywhere, followed by the disaster that was Vista.

They released Windows 7, and somehow then decided, yet again, to screw things up with Windows 8 because 'mobile'.

If only .NET was actually everywhere like Swift on Apple, or Java/Kotlin on Google land.

Instead we keep having COM with shitty tooling for the relevance it has on the OS API surface, especially since Vista.

Windows 2000 was the last version of the Windows NT lineage with Dave Cutler in charge of everything.

His no-nonsense attitude towards fixing known bugs was sorely missed in later versions as Windows quality began its decline.