Wifey B: Is it hot or cold? To someone from Anchorage or Duluth, MN, then it's hot I guess. To a bikini girl from FLL, it's freezing cold.
However, the PNW cruisers seem to love it there. Go look at some of the normal temps and see if they work for you. High today in Seattle is 62 and low is 47. FLL is High of 87 and low of 78. But heck no, don't winterize. Do protect it. Use it all the time if you can. It's more than fit for boating even if not for wearing a bikini. At 8 knots, you could cruise for years among the islands of the PNW.
Now, about going south. You're right, not the greatest trip. However, don't dismiss all the little towns between Port Angeles and San Francisco. Some interesting stops. You might get stuck somewhere for a while. Big deal. You get to SF and you have the entire bay and the Delta to explore. LA you have Hollywood and Beverly Hills to explore.
San Diego you have a great climate but not close destinations. Still a trip south from there takes you to a whole different world.
There's no right or wrong. Just do a bit of research of temperatures and rain and think of your tolerance. I can say this. I don't freaking like cold. But I can also say this. If I lived in the PNW my boat would not get winterized and I'd use it year round. This year, Jan 16-21 all days mid 50's, all nights mid 40's in Anacortes. You button and zip up the bridge, turn the heat on. By noon with heat through the windows you'll be turning the heat off and removing layers of clothes. It will be beautiful. Won't matter the temp outside, as you'll be inside, inside your toasty boat. We use to boat in NC in 40 degree weather during the winter, when we could. Incredible was boating when it was snowing. So, have fun.