Ohhhh great point about the max range on demoralize. I didn’t even notice that. Yikes. I will have to rethink my approach.
Also, the more I think about it, the more I’m thinking I will go with Gang Up anyway. My problem is that I like to try odd things with classes, which… as you pointed out, the current list of rogue’s rackets aren’t really designed to do at all 
So that sort of puts me back into relying on melee for most of my damage and using shortbow as a sort of situational weapon or possibly for opening attacks. I was hoping to perhaps use the shortbow to harass spellcasters too. Hmm…