I'm curious how one deals with pump outs? If the water is frozen around your hull and you're forced to use a bubbler how do you manage adding water to your boat (frozen hoses) or pumping out your sewerage?
For live aboards there are different answers, but for most sailors...
Pump-outs. If the boat isn't sailing, there is no sewage. As soon as the water is soft, the pump-outs are open. The key is to pump-out just as it gets cold, and to flush with a weak glycol mix as need be. I've never actually filled up.
Most liveaboards in this area use marina sanitation as much as practical in the winter.
Freshwater. Empty hoses don't freeze. Just roll them up or use jerry cans. freeze-proof faucets work all year. Easy enough.
Most years we get only light snow, though there are clearly exceptions. Shoveling a dock is a simple matter of pushing it off; it is not going to drift or build banks. However, I've never bothered. Certainly, even for the liveaboard, it would be far less than a driveway! As for decks, there is no point and it adds insulation. It's quiet too. Winter is when it is extra nice to have a hard top and enclosure; keeps the door clear.
----
Yup, depending on where on the Chesapeake you are, 0-6 weeks may be lost to sailing. It's more a matter of salt/fresh and tidal warming than air temperature.