If you're in Oregon, you don't need dedicated winters, unless you plan on trying to drive on freezing rain, which I don't recommend. It doesn't really snow enough to justify dedicated winters. I've been running different iterations of Conti DWS for the last 20 years, and I have literally never needed to chain up in the PacNW, and I live on a hill... Every year countless people leave their cars/suvs on the side of the road on our hill. I've even driven to Mt Hood several times when it was required to carry chains... My friends that were following me in their Ford Explorer got stuck, so I lent them my chains so they could make it into the parking lot. Honestly I think you'll be fine with the DWS 06 Plus. But I think they only come in 295 for the rears, and 265 for the fronts.
I don't know how the Pilot Sport AS4 will do in snow... I've run the Pilot Sport AS and AS3. They are nowhere near as good. Hopefully the AS4 are better. My coworker/neighbor has the same car I do, and he had Pilot Sport AS3 on his car, where I have DWS on mine... I've had to rescue him on our hill before, becuase he couldn't make it up the hill without chaining up. After two winters of that, he finally switched.
If you live in central or eastern oregon, maybe it's different, but I don't see the point in the valley... I don't understand the clowns running around in studded tires in the metro area from October to March....