My list is a bit smaller, but has some overlap. For all platforms (Linux, Windows, MacOS):
1. Sublime Text & VIM (for all things text)
2. Firefox with tampermonkey & ublock origin (browsing 101)
3. Everything (Uses it as my launcher and finder of everything on my computer)
4. Irfanview (must-have for everything image-related)
5. Classic Shell/Explorer (to get a usable winXP-like desktop)
6. Gamma Panel (Adjust brightness via keyboard shortcut presets)
7. O&O Shut Up (for same reason as you)
8. Autoruns (to disable all useless services & scheduled crap-ware in windows)
9. MSys (for linuxy everyday tools, can't work without 'em).
10. Conda (with opencv, torch ... for automation and graphics munging)
11. Winamp (For all things music consumption)
12. VirtualDub ("Irfanview" for Video)
13. MediaPlayer Home Cinema + ffdshow & LAV filters/splitter (Better VLC)
14. Avisynth (All things video processing)
3. Irfanview (must-have for everything image-related)
4. Conda (for heavier automation than bash)
5. Wine + (Irfanview, Virtualdub, Avisynth)
3. iTerm (for a usable terminal)
4 Homebrew (to get linux tools so I can work)
5. iStat Menu (to know what the heck my laptop is doing)
6. Conda (for automation)
(Haven't found a wine-variant for MacOS, so I have to make do with the shtty preview instead of irfanview. For Video stuff I'm forced to use Linux or Windows for via remote desktop).
I wish there was cross-platform install bundle that contained:
* Irfanview, Everything, Avisynth, Virtualdub, MPCHC with LAV filters
If someone aims to create such, that'd be awesome :)