Welcome! I think you'll find the Chesapeake has many advantages--protected waters, countless anchorages, access to cities and towns yet plenty of wilderness, and a year-round sailing season if your tough.
My blog tells of my experiences, as well as some useful links on the side bar: Sail Delmarva
Ice is a significant problem from Annapolis north. In Deale we freeze in for a few weeks. From Solomons Island south, very little ice.
High wind is a matter of perspective. I suggest you check a weather site and make your own judgment. In general. there are seldom more than 1-2 high wind days in a row, with several calm days between them. Waves seldom get large because of the limited fetch.
Traffic can be considerable around Annapolis and some parts of the northern Bay around holidays, but other than that is minor.
Anchorages are countless.