I'm somewhat reluctant to sound off on this thread, as it's a bit open-ended for my taste. But here goes!
Given the dearth of cruising literature extolling the the coastline between the northern tip of Washington State and mid-California, it should be apparent that this stretch of water is NOT a "cruising destination". In addition, a casual glance of pictures of ports of call between these locations will reveal a significant lack of pleasure boats. Both should be a clue that the notion of making a voyage in either direction along this stretch of water might be better thought of as a delivery, vs a cruise. While this is a bit of a generalization, the notion that a retiree, with no schedule, can and will be safe and comfortable on this part of the ocean, given sufficient patience and a well-found vessel, and can thus routinely venture upon these waters with impunity is naive and disingenuous. And why is that?
Well, EVERYONE has a schedule! If you've ever been stuck in Neah Bay (for instance) for a week awaiting a weather window to go southbound, when the big event for the week is a Wednesday night high school basketball game, you've visited the Cultural Center several times already, you've read every book aboard multiple times, and even the local Coasties and rescue tug crews are bored out of their gourds will convince you that the sooner you can get off this stretch of water, the better.
If you've ever had to lay over in Coos Bay on the transient dock that the locals love to crab from, leaving their beer cans and crab guts behind, and a LOOOOnnng way from anything like a town with something to entertain yourself with while waiting for some event like the prevailing howling northwesterly in the summer to lay down will provide reinforcement of that notion. If you've ever had to hike from the transient docks at Bodega Bay (again, waiting for a weather window to get around Cape Mendocino) for a dinner on the town (something like 3 miles R/T) will reinforce that notion.
I have made passages from SoCal to the PNW multiple times, aboard typical "coastal cruising powerboats", at many different times of year. I've made these trips as both multiple day-trips, and long-distance 24/7 deliveries. And they've NEVER been other than as DDW expressed it so well-a game of russian roulette. Sometimes you're the window, and sometimes you're the bug, and I've landed on the loaded cylinder several times, often multiple times during a trip. And conversely, I've had trips where there was seldom even water on the windshield. You pays your money, and you takes your chances.
Planning for a routine "north in the summer, south in the winter" snowbird gig on a pleasure boat along this coastline is certainly not for me. YMMV, and anyone is certainly welcome to have at it. But talk to the professionals that run this coastline (Pat Raines comes to mind), and heed their advice. Life's too short to practice bleeding before cruising, and I've done my share of bleeding along this particular stretch of coastline.
Regards,
Pete