Hey, billy013. Best avatar of all time!!
Yeah, I'm out there several times a week myself. In my opinion, no, we do not get enough even toward Gresham or The Gorge (these two areas tend to be colder than the rest of the metro area and sort of have their own weather). It does happen, but there is always fair warning, It is virtually never a surprise. So, you may just have to drive that day. Or, when we get serious ice (every so many years), there will be no work. The city just shuts down.
Anyway, welcome to P-Town. I grew up here, then went away to school/training for 16 years and then came back to take a good job. It has changed a lot. Much bigger. Pretty good for cycling, though. I do miss aspects of NYC and the South. Boston, though you can have it this time of year. Anyway, I hope you get settled in. If there is anything I can answer for you, just let me know.