We have not hauled out boats in the Chesapeake. We've always had them in sheltered marinas where they were protected from ice 'flows" in the years when the creeks freeze over. (If you had an exposed slip, that might not be a good idea.)

Having said that, sailing beyond November or before March (something) can be pretty tough. This year, there were people sailing intermittantly through the end of they year (beyond Frostbiters).

If you're comparing cruising grounds, the Chesapeake (especially in the mid-Bay areas) is hard to beat in the mid-Atlantic areas. Air conections to Baltimore are easy and relatively inexpensive. The marinas aren't inexpensive on the Western shore.