Honestly if you’re going to be living in your van the PNW would be the place to be the temps stay for the most part pretty moderate (if you don’t mind rainy muggy weather) and there’s a handful of places where you can both ski and work!
I’d look to places like Portland, Eugene, Seattle, Bellevue, Tacoma, Medford, Vancouver WA.
WA has better skiing than Oregon by far and you’re more likely to get paid better there.. but Oregon is pretty kick back, the type of place you can settle down both states have great people and they are good places for homeless people.. as in you won’t get persecuted too severely by the law should you choose to be homeless (although I still wouldn’t recommend it)