We turn our water on a few days after ice out each year. Pipes above ground. On stilts. All plastic pipe. (I think this helps) We religiously turn the power off to the pump when we leave. We have had a few experiences where the outdoor shower would not run because the pipes were frozen. I took that as a sign it was probably too cold to take an outdoor shower. Have never had a problem.
I think the bigger risk is the winter draining, which you seem to have figured out.
Welcome to the Forum. Happy retirement.
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