Any suggestions? Would be nice if there's a good SWE job market there, but I suppose with the possibility of working remotely that's not a make-it-or-break-it aspect.
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.
Also, Portugal, Lisbon, world class surfing from the city, amazing rock climbing all over Portugal and Spain and Skiing in Northern Spain/Andorra or Southern Spain Sierra Nevada. Not sure about Skiing in Portugal itself.
* In Colorado, Boulder is minutes from fantastic climbing. It's about 45 minutes from alright skiing (Eldora) and 2 hours from great skiing in Summit county. Golden is closer to Summit county, and still close to climbing, but the climbing isn't as good/diverse.
* In Utah, you can do some river stuff (not traditional surfing) in Moab and the climbing is darn good. You can also live in SLC and you are 30-60 minutes from climbing and 15 minutes from Alta (depending where in the city you live) which I hear is world class.
Boulder, Denver, and SLC all have great SWE job markets.
I don't know any place in the USA that has all three. Maybe Hawaii (not sure about the climbing, but I've heard of folks skiing in the morning and surfing in the afternoon)? Maybe southern California?
Los Angeles, Orange County, or San Diego county (So-Cal) if you prioritize better surfing locations than skiing.
AFAIK, only these two will have good locations for all three activities in the US.
Climbing in Acadia and the White Mountains, surfing on the coast, and skiing at Sugarloaf or Sunday River (or the white mountains).
Surfing and skiing were hardly world class, but both sports are locally popular and have a decent community following.
South America on the Pacific side will get you good winter surfing, and the mountains will provide ample alpine sports. Europe in general has some excellent ski/climb mountains, but I'm less familiar with surfing. Maybe France on the Atlantic side?