Hello JackAdamMiceli,
Thanks for using Apple Support Communities.
From your post I understand that when you try and either stream your Apple Music or play what is made available offline, it will just skip the song. To start with troubleshooting this issue I suggest that you sign out of your Apple ID in iTunes, sign back in, and then enable Apple Music with iCloud Music Library.
Choose Store > Sign In (or Sign Out).
iTunes 12 for Windows: Manage your iTunes Store account
- Make sure that you're signed in to iTunes with the Apple ID and password that you use for your Apple Music membership.
- Mac: From the menu bar at the top of your computer screen, choose iTunes > Preferences and turn on iCloud Music Library.
Windows: Press Control + B on your keyboard to open the iTunes menu bar. Choose iTunes > Preferences, and turn on iCloud Music Library.
- If you already have music on your device, you'll be asked if you want to Merge or Replace the music. Choose Merge to add the songs currently on your device to your library.* If you select Replace, the music on your device is replaced with your Apple Music library.
Check your Apple Music library settings - Apple Support
Have a good one.