I guess a third of a mile isn't really much and I'm making it too big of a deal. I've climbed longer and steeper hills with a standard crankset. I'll admit climbing is my "specialty" as a road cyclist.
The cooldown lap is a good idea. I don't think I would have thought of doing that.
I guess I'll just have to HTFU in mid-August and just do it. I'm hoping the temperatures will fall a bit by then. It's been awfully hot lately.