In an area where temperatures go into deep freeze for about four months of a nine month "camping" season, I never found it a pain to winterize. Protecting the plumbing from freezing before going into storage was at most a 30 minute job, and "dewinterizing" added less than 30 minutes work to the day or so of trip prep I would do each time I came out of storage, no matter what time of year.
So to make use of these fringes of our extended season, and to prepare for winter trips further south, it was not unusual for me to winterize and dewinterize four times a year or more. Not costly, not time consuming, and not particularly wasteful. If I don't dump my fresh water tanks before storage (e.g. in summer) I always dump and refill coming out of storage, to get freshly chlorinated water into the system.
I don't know what people in your area do, but the sort of temperatures you are talking about are what I expect October and November, March and April, which are my fringe months. Winterize to store, dewinterize to camp.
