One other thing to note is that when you do hit the second hotkey, your order will look like a range order (see picture below). This is actually visually showing your "fill up to" range (Thanks for explaining this Kyle!)
This is a little embarrassing, but I think I had this hotkey working quite awhile ago, I just didn't understand what I was seeing! I thought it was some kind of weird range order, that the script wasn't working, and so I always cancelled it before triggering and went back to the drawing board!
And just going to tag some people who I know were interested in this in another thread:
@Travis Weirich @peterB @JenniferL @WindssKat @Ryan Wilson