7 and 2008R2 were pretty good too. All downhill from there..
"The 64-bit versions of Windows NT were originally intended to run on Itanium and DEC Alpha; the latter was used internally at Microsoft during early development of 64-bit Windows. This continued for some time after Microsoft publicly announced that it was cancelling plans to ship 64-bit Windows for Alpha. Because of this, Alpha versions of Windows NT are 32-bit only."
https://pubs.opengroup.org/onlinepubs/009695299/functions/sy...
This is all a guess, the POSIX subsystems were a bit before my time and I've never actually used them. I just know how symlinks work on Windows/NTFS and when they were added.
The only issues I came across were artificial blocks. Some programs would check the OS version and give an error just because. Even the MSN Messenger (also by Microsoft) refused to install by default; I had to patch the msi somehow to install it anyway. And then it ran without issues, once installed.