This section on OS/2 explains why MS ended up with two incompatible Windows families, one a real 32 bit OS and the other not (Win 1, 2, 3.x, 95, 98 Me) and why NT in 1993 starts at NT 3.1, because it was really a sort of MS OS/2 Version 3.1. The Windows 2000, XP, Vista and Windows 7 are all actually versions of Windows NT 5.x, and Windows 8.x is really 6.x and Windows 10/11 should be NT 7.0 and 7.1.
https://en.wikipedia.org/wiki/OS/2#1990:_Breakup
Actually it unravelled before 1990, sometime in 1998-1999 as I actually maintained a system with MS branded OS/2 in 1989. By 1989 MS was selling MS OS/2 as a server for networked Windows PCs using NetBEUI and LanManager.
Apple stopped incrementing after replace Mac OS 9 with Mac OS 10 aka Mac OS X about the time NT 5.1 (XP) came out. Now each version is just the first digit after the 10.
See also crazy MS Office and MS Word numbering and naming.
Totally crazy is Browser Versions.