"The Cage" = Windows 1 --> The very first version. Very rough.
"Where No Man Has Gone Before" = Windows 2 --> They made some refinements.
TOS = Windows 3 --> This is the first version Average Joe is familiar with.
TMP = Windows 95 --> Took everything to a new level.
TWOK-TUC = Windows 98 --> Worked out the kinks from before.
TNG Seasons 1-2 = Windows ME --> Lots of bugs.
TNG Season 3 through ENT = Windows XP --> Became the new standard. Then stuck around, stuck around, and stuck around. It refused to die after it was long past time. Each new series is a new Service Pack.
Kelvin Films = macOS --> It's Apple! Plus, they were made during the Paramount/CBS Split. So, during this time, Paramount was like Apple, and CBS was like a PC.
DSC and PIC Seasons 1-2 = Windows Vista --> Very divisive and the people who hated it were very loud about it.
SNW and PIC Season 3 = Windows 7 --> They tried to make a version that would be better received. Some people still stubbornly stick to XP.
SFA and other Upcoming Projects = Windows 8 --> A lot of people will be like, "What the Hell is THIS?!?!!!" I'm calling it now.
That’s genius!