I found that if I check “Cursor” change it to Hand, the mouse cursor correctly changes to a hand when hovering over the element. Continuing from that, I then bound a new function to the Tool Tip Text, and found that it correctly hits the breakpoint I placed on that newly bound function.
From there I manually created a Widget(as described in Rama’s Tutorial) and added a “Set Tool Tip” node, inputting the newly created Widget into that node.
This successfully created the tooltip at run time when the mouse hovered over the appropriate element.
Im going to go ahead and post this in the bug report category.