I took a look at your blog. Our paths have probably crossed a few times. My boat is on Lake Union, We head out to Blake Island often, and my parents live near the Brownsville marina so we head there often for boat projects.
I too have spent a lot of time learning the hard way; being under full sail, heeled over with the motor at full throttle waiting for the tides to change to slip through Agate pass was a memorable one.
Trial and error has worked pretty well so far. I just spend time going over the events and thinking about what could be done differently next time.
If you ever want to sail on the lake after work, or just grab a beer and talk sailing send me a PM.
See you around, I sail a Westerly 23, white topsides, black hull and red sails.