The iTunes application on a Windows PC is not user-friendly and has bugs…
The iTunes application for a Windows PC is very poorly designed ('clunky' is the IT technical term - very few things are intuitive) and has numerous bugs. For example: I loaded one of my own CDs (not purchased from Apple/iTunes). It couldn't find the track titles, so I edited each track to add track title, etc. But when I copied the tracks to a 'Playlist', all this information was now missing. I tried to sync from iTunes on my PC to an iPad. It took about 20 minutes while it said it was syncing with the device, but then it did not copy all the tracks in all the playlists to the iPad. After a few time-wasting attempts, including starting all over again, I took the advice from other iTunes reviews to install VideoLan (well-respected media playing / conversion software) on my iPad. Amazingly, the iTunes application for the PC provides a very simple and reliable utility to copy iTunes playlist files to the VideoLan app on the iPad. So I only use iTunes on the PC to load CDs, copy the files into a 'Playlist' and then use their own utility to load the files into Videolan on the iPad. Simple. Works every time.