Jaalex, if you are fine with the drive then the Chesapeake will knock your socks off compared to Iowa sailing.
Folks have been posting about "bonus days" of sailing in October. I consider this a little silly. October is prime sailing season on the Chesapeake IMHO. No insects, doldrums or thunderstorms. Nice temps, steady winds, and tons of rockfish.
I consider someone else's claim that the Chesapeake has year round sailing season to be equally ridiculous. Jan and Feb are tough months to go sailing. But we do usually get a couple warm spells when you can take the boat out for a day sail in winter.
Good luck in the job search!
Gemini Catamaran Split Decision