What would happen if the Chesapeake Bay area was struck by a Major Hurricane?

All the facts that you mentioned are true for the most part. The damage of the Chesapeake Bay area would be similar to New York City and Long Island. The storm surge would cause significant amounts of flooding and damage because of the many coastal locations. Evacuation probably wouldn't be that bad because of all the different directions you can go. The other questions you asked really can't answer until it actually happens and where it makes landfall. The most damage will probably be caused by storm surge. It probably wouldn't be that bad when it gets to D.C. because it's inland and hurricanes usually weaken by the time they get there. The next one that affects the Chesapeake Bay will probably be the next one from NYC because most storms usually travel along the coast.