This isn't my jeep (don't have access to it at the moment), but here is an image of a JK with a Rock Hard. I've put a circle where my electric connection is. Do you think it will reach to that point?
My electric is mounted in the grill opening, second slot from the left looking at it (passenger side) and air is in the next grill slot. Localish RV shop that installed for me put it there rather than cutting hole and mounting in bumper.
Yours looks like it has quite a bit of slack in the electric, but can't tell if it would reach all the way across and up, and still have slack in the turns.
Interesting on the riser. Not sure if it's the difference between stock and Rubicon (can't tell if yours is a JK or JL) or between the LE and regular ventana, or Freightliner vs. Spartan, but I don't have a riser and it's nearly perfectly level.