OR CCW is pretty easy. Only marginally more difficult than the WA one. You have to take a short class about where you can carry and shit like that (which can be online) and should only cost like, ~$30. Then you will receive a certificate which you bring with your ID, letter stating your "need" (could be pretty much anything, including living close, or working in OR), and finger skin over to a OR sheriff office of your choice after arranging with said sheriff's office for an appointment.
The area overall is very gun friendly, both WA and OR. Though OR is still more NFA friendly. WA you can have SBR's, AOW's, and suppressors. In OR, you can have any NFA.
As far as living in WA and working in OR, well, I currently do that. IMO, there's no real reason other than liking the particular neighborhood or whatnot. You still have to pay OR's income tax. And if you shop near your home, you will pay WA's sales tax. I mean, if you get a job at PDX, it may be easier to find a non-shit, non-super expensive, neighborhood on WA side close by than on OR side.
There's a couple of other airports in the area as well. Dunno if you work on the big jets or not. But Hillsboro airport is also a huge one, though mostly cargo instead of passenger like PDX is. There's also Troutdale airport a little to the east of PDX. It's much smaller though. Plus, a smattering of tiny airports lying around.