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I actually live in Portland and I commute 15 miles each way. I drive a SV650- nothing added. I just drive much more reserved when it is wet. When it rains hard you have to worry about leaves and branches on trees, but I assume that is something everyone has to deal with. We have about one ice storm a year. The thing to worry about is the gravel laid out after the ice storm. It takes weeks before it is clear again, so ride VERY carefully then.

Good rides... well, if you want to go for a longer ride, head up the gorge and then tuck back on some back road there. For short area trips, explore Skyline BLVD area and out to the North Plains. There are some good curves in various spots and the traffic isn't bad if you go at the right time of day. Hope this is somewhat helpful.
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