I heard you say you are going sailing in SF bay. I took sailing lessons in Santa Cruz and really liked it there except the mooring has a long waiting list and is expensive. I've heard that the sailing outside SF bay is intense! The winds are pretty consistent and it requires some advanced skills. When the wind is blowing hard and the seas are up is when you realize how insignificat we are in comparison to the ocean.
I owned my last sailboat for around 7 years and did a lot of sailing in the lower Columbia river and along the coast up into Canada. I had to sell it a couple years after the kids came along because I just did not have the time to drive to the coast and maintain it. When the kids get a bit older, I hope to get another sailboat. It is a great beach house to stay at even if you stay in the harbor. I love harnassing the free wind power and hearing the crash of the waves agains the hull. Waking up in the morning in a cove on the Oregon coast that my dog and I had to ourselves and observing a grey whale swimming around my anchored boat is something I will always remember. I hope to teach my kids sailing and seamanship.