iTunes makes me log in multiple times every time I launch iTunes

I don't know exactly when this started (within last few months), but now every time I open iTunes, I get 3 or more password prompts in a row. The first one tells me to sign into iTunes store. If I enter my password, I get another prompt telling me my iTunes Store session has expired. If I enter my password to that I get another sign into iTunes Store prompt.

If I enter my password once, I can cancel the remaining prompts, but if I cancel all the prompts I can't play any music from Apple Music.

Things I've tried which didn't fix the problem or made it worse:

1. Signing out of iTunes Store, closing iTunes, opening and signing back in.

2. Deleting iTunes music library files.

3. Deleting some files from C:\Users\username\AppData\Roaming\Apple Computer\iTunes (made things worse as the password prompt came up continuously)

4. Deleting some files from C:\Users\username\AppData\Roaming\Apple Computer\cookies

5. Deleting some files from C:\Users\username\AppData\Roaming\Apple Computer\Preferences

At this point I have no idea what else to try. For whatever reason I need to enter my password three times any time I close and reopen iTunes.

Any ideas how to fix this?