West Coast Weather Planning

[Charlie]

Not sure if this belongs in Navigation.


I plan on bringing Ohana down the coast from Astoria OR to SF Bay in the middle of May. We have flexibility on leaving later but don't want to leave prior to May 12 b/c I don't want to leave before Mother's Day.
It has been years since I planned an extended trip. With all the new technolgy I'm at a loss for how to find a weather window. I've been looking at PassageWeather everyday and plan on reading the NOAA weather forecasts now that the trip is two weeks away. I've emailed the Weather Guy out of Hawaii but have not had a response. Looking at the 500 mb charts It looks like the best time to leave will be when there is a high west and south of the Coast. When the 500mb lines are near parallel to the coast then it makes for a good run down the coast with 10 to 20 knots of wind off of the rear qtr. In looking at the Costal Pilot and the pilot charts May is a good time to do this as the summer pattern is usually set in. April there is a good chance of southerly winds and fairly strong. June would be better but I need to get the boat closer so that I can get her ready for Mexico. Does anyone have advice on how to pick a weather window?