Hi AmazedHuman,
Welcome to Apple Support Communities.
It sounds like you’re running into an issue managing the content on your iPod shuffle because of the new iTunes features. I understand it can be frustrating when things change or become too complicated, but you can display the sidebar and continue to navigate iTunes like you may have in some of the previous versions.
iTunes 11: Frequently used features
Show or hide the Status Bar and Sidebar
In iTunes 11 you have the option to turn the Sidebar and the Status Bar on or off; they are off by default. To do this in the menus, go to:
Show Sidebar - Choose View > Show Sidebar (this feature will display iTunes features on the left side of the application including Library, Store, Shared, Genius, and Playlists).
Also, the article below will walk you through displaying your iTunes Store purchase history.
See your purchase history in the iTunes Store
I hope this helps make the new version of iTunes a little more enjoyable for you.
-Jason