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In my experience (having travelled the world looking for this place for a dozen years at one point) is that you're not going to find all 3. Even two is tough if you want them to both be world class.

Santa Barbara might come close, with Rincon point right there and the Brickyard and other good bouldering just up the hill, and weekendable skiing on the other side of the state.

Portland worked for me for a while, with a good mountain and decent (cold) waves each 90 minutes away, enough cragging around town to fill summer after-work sessions, and Smith Rock there for weekends. But none of those places will have people travelling halfway around the world to visit just for the climbing/surfing/boarding.

And that's the thing. I didn't want to settle on any of this stuff, so I made tradeoffs. For me, that meant setting up shop in Fontainebleau, France, with its lifetime supply of world class bouldering. It has direct flights to Lisbon and Agadir for short surf trips, and working remote means one can simply decamp to Puerto Rico and a quick 10 weeks of winter surfing.

The idea is to pick the most important thing (which is allowed to change over time) and set up shop there. Snowboarding got deprioritized from the 3x/week status it held when I lived near Mt. Hood to just 1-2 weeks/year in the alps. Surfing happens in longer, more frequent chunks, but more often tends to happen in tropical paradises that don't involve 5mm of rubber and a hood.

That's the cool thing about working remote. You can be as remote as you like.

Good luck!

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