IC40 - Sanity Check on 120V Wiring

In all honesty, gentlemen, I am fairly intuitive with 120V circuits. I'm not an electrician but I know enough to diagnose and troubleshoot. I have 0 experience with 240V circuits, which is why I suspect this one threw me for a loop. (behavior wasn't making sense to my simpleton 120V brain)

I want to let you know that your help hasn't fallen on deaf ears. I have the winterizer in place now, so I'm not in a hurry. I will do my due diligence and make my usual list of steps and materials needed to swap out the switch and wiring correctly, and if I don't feel comfortable doing it I will hire an electrician to hop out and knock it out for me.
 
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