Saw a thread on the eight forums that might help me but had some issues with merging...
Solved Getting back 'Empty Recycle Bin' Context Menu On Recycle Bin
So apparently a program I uninstalled that had some controls over my Recycle Bin (from IObit, what garbage) has now corrupted my recycle bin so that I can't 'Empty' it. The context menu just shows the entry "empty" just like that, not even capitalized, where the Empty Recycle Bin used to be.
Also, when you're inside the Recycle Bin, the 'Manage' option on the ribbon is missing. I can empty it via cmd prompt and via CCleaner, but I want the original functionality restored.