[Zeke]

The main draw to areas with very high real estate prices are weather and job market. You can eliminate the latter. So, now you can look at areas that have a dismal job market with high weather desirability. Small communities will offer this if not totally bucolic living on a lake or oceanfront property. That brings the price up considerably.

You mention airbnb so it has to have something to offer to those that are looking for a place to stay while checking out the local scene. IDK much bout OR so I can't help there. San Juan Islands may be pricey but there are other areas with similar weather.

If you want to get "out there" you could think about CA high desert. Lots of sun, no visitors unless you're in proximity to Death Valley. Palm Springs is not hot in the winter. 84 today as SoCal is experiencing a 2 day heat wave. Next week PS will be in the mid 70's. For all of the next 3 months PS will be about 70, clear with chilly nights. Little to no rain. Death Valley a little cooler days and nights for comparison.

Out where Marv Evans (shoot him a PM) lives in the San Diego County rural areas you will find cool winter weather with higher elevations being cold. Not sure what draw there is unless you can connect to something about horses and that sort of experience. There are some good day trips from there.

Where I live winters are mainly mild, but we do get weather, especially in Feb and March. It's very crowded so unless you picked up a condo near the beach and marinas, nothing going on. We do get really high rents during the Grand Prix with some rentals getting a month's worth of rent in a short week. Lots to do on and about the water (ocean) and Catalina Island (which would be ideal but the real estate is dear).

Lastly, Ventura County offers a lot. You'll just have to read up on places like Ventura and Oxnard. Very picturesque. Lot of farm land of you want to get out of a city. Good golf too, just like PS.