iTunes keeps resyncing the same 49 songs

To be clear you've made sure that the work and movement fields are all empty for these tracks and the Use Work and Movement option is not selected for any of them. Another possibility if it isn't data in the work and movement fields is that you have some logical duplicates, where the same file has been added to the library two or more times. See Duplicate songs in iTunes - Apple Community to eliminate any duplicates.

tt2

Hey there BloodyApple,

Thanks for reaching out to Apple Support Communities. We understand that you're having issues syncing music. Here are resources that can help:

Sync iTunes content on PC with your devices

Specifically here:

Keep items from being automatically synced

If there are some items you never want synced (for example, if they’re too big to fit on your device), you can keep them from being synced.

You can also turn off automatic syncing for music, movies, and TV shows. You must do this if you want to sync iPod classic, iPod nano or iPod shuffle with more than one iTunes library or automatically fill your device with songs using Autofill (see the next task, below).

Note: iPod classic, iPod nano and iPod shuffle are supported using iTunes on Windows 7, Windows 8 and Windows 10.

Keep us posted.

Have a great day!

I'm having the work and movement field issue and I can't fathom why Apple would have introduced work and movement, which are extremely useful for classical music fans, if they basically break sync. It's so frustrating to have the classical music I've got on my iPod Touch resync every single time I sync anything else.

Beyond me too.

tt2