Since you gave more detail, I think I understand your question a bit more.
You can dewinterize and winterize again with no problems. We winterize at least 3 times every winter, as we take a trip to Florida in December and then again in March. And we sleep in the camper (driveway camp) all winter long too.
It only takes a few minutes to winterize. I think it takes longer to un-winterize, to flush out the pick stuff, I think takes longer than pumping the pink. Nothing wrong with setting up the camper for a couple jonts before cold weather settles in.
Have the previous owner explain how to winterize, step by step. Make sure they show you how to by-pass the water heater, and you'll see winterizing is not a big thing to do.
You also have the option to blow air through the lines to clear out the water, and then run the pink later, if you are concerned about freezing before you have to finally park it.