I would not give up hope but I would financially & emotionally plan on it being empty for an extra month.On the west coast you are not fighting against weather, just against busy-ness and distraction of the holidays.But I would argue that many people want to look when they have more down time the week between Christmas and New Years, if your PM is working. 

So, my question is this.....How many landlords would be willing to pay a monthly fee that guarantees regular standard upkeep of their properties, including general repairs, with only additional costs being any parts or materials needed to complete repairs or replacement, weatherization of pipes during the winter to protect them from bursting.

Add that to a cool climate, SF has among the most desirable weather d geography in the world, so it seems a “hold” even if it’s a softer “buy.” 

While we do take precautions for freezing weather and the plumbing, I don't actually know of anyone who has had a pipe freeze and burst.

Our accountant is very resistant to setting up children's payroll though, so I'll look into it myself or ask a different professional. 

I have already been hit with a few snow storms and the (really) cold weather is coming in this week.Any thoughts would be super helpful!

Is the owner resistant in providing?

With regards the legality of the wholesaling of property in FL:Those waters are very grey on weather or not you need a license to legally wholesale a property. 

Normally banks resist allowing that access, but if you press you can generally speak to them, or to their supervisor.

You could not control the bomb cyclone, I feel it would be a tiny settlement due to the fact you owe no duty to prevent extreme weather.