This will work.
Thanks for the confirmation. I did another dry-fit today to check the lengths of all the wires I have and figure out what lengths I need to make the above system work. I need to get 3 lengths of Di2 wire(150, 500, and 1000mm), the EW-WU111, (2) JC41 boxes, and the BT-DN110 battery.
The stumbling block I'm on now is running the wires from the aero bar extensions internal and through the whole that are in the mounting blocks for the arm pads. They're just a touch too small. It looks like they're about 5/32 and they need to be 1/4. I'm debating if I should take them to a machine shop or if I should cut the plug off the wire and reconnect. I've heard bad things about cutting/splicing Di2 wires.