Hello Ben,
I have been actively researching farming in the PNW(WA and OR) for quite some time, and have lived here for about 15 years. I came here with $1000 and 2 boxes of belongings, but have found many opportunities here through the years. I'm sorta kinda planning making "the jump" in the next 2 years. The summers here just can't be beat, and I have found the winters to be ok as long as I stay active and don't let the rain stop me. Get some muck
boots and decent raingear and you're good! Also, PNW beer is very hearty, strong, and deliciously hoppy! The major obstacles to making the jump for me so far are regulatory agencies(just learning all of the codes and regulations I must comply with and the fees!), OR's water regulations appear more strict, generally, than those of WA. If you cannot find a place with water/irrigation rights, in either state, do not despair. There are perfectly legal and creative methods, conservation measures etc. discussed elsewhere supported by both states. One other obstacle, obviously, is access to decent agricultural land. I think OR beats out WA (at least in the Western portions) in this respect. WA glacial soils can be tricky to deal with so
permie practices are perfect around here.
Populations of both states are highly educated, and, at least in Seattle where I live, there seem to be plenty of people with plenty of money, and willing to spend it on quality food/natural/local products. Even the PhD barista types spend their money on good food. Oregon seems to have more resources, and certainly more "permaculture-type" people, in my opinion. I can't wait until we vote for GMO labeling next week in WA though!
Lastly, I'd personally avoid areas with large military bases/populations. Also there are areas of the PNW where large coal terminals are being proposed, like near Bellingham(love Bellingham!) Longview, maybe Coos Bay OR so keep that in mind.
Best of luck and keep us posted...The PNW is a wonderful place to live and we need more people like you here.