Just around the last week of November / first week of December we had a crazy cold snap in the Puget sound that pretty much froze everything. So if your TT wasn't either winterized or well heated, it was probably gonna need repairs. We don't get a lot of below-freezing temps that last long enough to matter, but those snaps take many by surprise when they come, and that's when the fun begins.
Thus, as a new owner anxious to protect the investment, I opt for choice #1 (winterize and weekend camp in our aluminum tent from time to time until the spring). No water anywhere inside the TT's plumbing until then - and that includes the tanks. I don't want a cold-snap surprise while it's in storage between trips.