I personally have a difficult time staying anywhere for longer than two weeks..
I've tried wintering for a few months the last couple years, but that's always been spotty. This third year into my travels, I made the decision to winter for at least 4 months, to try and handle some business that means necessary to hunker down for longer than I usually like.. but yeah, I'm off the road for a good chunk of mid november- late April; is what I've come to prefer. Just because being stuck in the cold fucking sucks, but so does being stuck somewhere you dislike, just because it is warm.