Andrew could offer insight here as he sails a lot these days. Summer (Memorial Day to October) is light air followed by a huge thunderstorm. Fall (October to December) is really nice but variable temp. Winter (January) can be cold (50s) but still usually has wind. Spring, February to June 1, is IMO the best season and typically very reliable. Actually, it's all good.

The real trick is to only pretend to work so you can sail as often as Andrew does. That way bad air days don't get you down. He said 59 degrees and blowing 25 on Sunday but he sailed anyway. A bad day sailing is better than a good day at work.