iTunes Syncing Issues

Hi All

Recently, I have been having multiple issues with iTunes, which may or may not all be related...

Firstly is when I sync music to my iPod Touch, just about every time I get 'error 54', and don't know how to remove it. Last night I went as far as completely un-checking all songs/albums/playlists and still I got that error.

The second error that I receive is that there are duplicate file names, not exactly sure what this means, but it was popping up.

Finally, my third issue is that when I sync my music not every song actually copies over. On my iPod it shows that they are 'there' (not greyed out, they look like every other song) but yet when I go to play them they just show up as 'Not Playing' at the bottom. I've found that sometimes they need to actually be 'Deleted From Library' on my iPod to actually remove them!

Anybody got any ideas I could use?

~Adam

iPod Touch 6, iOS 11.3 / HP Windows 10 laptop

yncing etc