Old software

iTunes

7.2 first oldest version of iTunes to function (probably because it's the first with Vista support), doesn't connect to iTunes store, supports Audiobooks (needs to be checked in Preferences)

7.3.2.6 (last version for Windows 2000) appears to work and be stable and has a slightly different GUI where the selected menu option is blue instead of grey

Troubleshooting

For the "itunes.exe has been set to run in compatibility" prompt on startup, find the regkey (Computer\HKEY_CURRENT_USER\SOFTWARE\Microsoft\Windows NT\CurrentVersion\AppCompatFlags\Layers) and delete the one with iTunes. For me, Last.FM added it.

Computer\HKEY_CURRENT_USER\Software\Microsoft\Windows NT\CurrentVersion\AppCompatFlags\Layers

remove items from add and remove programs

Computer\HKEY_LOCAL_MACHINE\SOFTWARE\Classes\Installer\Products

also remove manually all folders, Common files application support etc.

iTunes 7.4 CD configuration error on startup, just create an empty folder named "CD Configuration" in the iTunes folder in program files

I've spent a lot of time on iTunes in my life

https://www.theiphonewiki.com/wiki/ITunes

https://ipsw.me/iTunes

C:\Users\scrip\AppData\Roaming\Apple Computer\iTunes\iPod Software Updates\ iPod_25.1.3.ipsw iPod photo

FileBot

Useful for renaming tv shows and movies by querying theMovieDB

Oldest free version is 4.7.7

Install. Likely will get warning that Java Runtime 1.8 is required. Download Java SE 8 JRE

Use TheMovieDB for both movies and tv shows