I just moved to Portland about 18 months ago from Northern Arizona. We live out at the edge of the east side (Troutdale), where weather is generally regarded as worse than Portland proper.
Most days are mostly overcast, but there are regular breaks for 3-4 days with clear sunny skies as well. I don’t find the weather that bad, but my wife has a little more trouble with it. It doesn’t bother me because I’m one of the few people actually enjoys the rain and I love the greenery you never could hope to have in AZ. I think your definition of rain matters also; for me, ‘rain’ meant “heavy, drenching monsoon-type downpour”, but we rarely have rain like that up here. Mostly it’s just a slow off/on drizzle, I usually don’t even bother to bring a rain jacket or umbrella when I’m around town. Sometimes it does get fairly cool though, days in the low 40’s with showers are fairly common.
Temps can vary wildly, mostly in relation to clear/cloudy skies. Wednesday morning we had iced up cars and roads and today it was in the high 50’s. They do get some occasional snow here, but it’s so infrequent that it tends to snag things up even when it’s only a couple inches. I can see how 8 inches would shut the city down.
Summers are awesome and it can stay light from about 5:30 to 10:00 or so, which makes up for the comparatively dark winters. The weather is definitely warm enough to allow for sleeping in a hammock all night with shirtsleeves and shorts, at least IMO. I love that OR has four distinct seasons, compared to the two I got in AZ.
One thing I will note (and my wife has noticed this also), is that people in Portland (and Oregon in general) love to complain about the weather. I can’t tell you how many times I’ve had this exact conversation:
Oregonian: So where did you move here from?
Oregonian: WHAATT?? Why on earth would you ever do that?? You must be hating it up here! I can’t believe anyone would move here from such a great climate, You’d have to be crazy to do that!..etc
Me [trying to be polite]: Yeah, I guess it is pretty rainy sometimes… So how long have you been here?
Oregonian: Oh, my whole life. I wouldn’t live anywhere else. There is literally nothing in the world you could give me that would make me move away.
Me [to myself]: Then why the hell are you making it out to be so terrible?
We actually have a running joke about who will get the “weather exchange” most in a single day.
I’ve heard (as a joke) that people up in the PNW exaggerate how bad the weather is as a means of keeping everyone else from finding out how sweet it is up here. Maybe they’re all just mad because we broke the code and came up anyway. I can confirm that it still works against in-laws; mine “can’t stand the rain”, so they refuse to visit except during July and August. They’ve never even bothered to ask us how the weather actually is, they’re just running on the idea that it’s completely miserable the majority of the year.