Yep, I am aware of the motor position, just didn't want to put in the work when I received the winch because I was antsy to get my boat on the water and good seemed good enough.
I did call their support at the time and ask them, specifically about the roller guide and the angle the rode was going to go across it, if it was ok to mount in that configuration, to which they said 'absolutely'. I think you could be right, I am going to add the project to my winter list of todos (growing by the day) and even if it doesn't solve the problem I think it will still be a win to reduce that angle and have a straighter run from the roller to the drum.
As for switching the wires, I don't think it's that simple for the rebel winches. Since the clutch for the free fall is integrated, unless that is disabled I don't think you can switch the motor polarity at will, as it would just free fall any time you wanted to pick it up and would be strictly power down. That trick would work on any of the non-free fall ones tho.