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
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