Getting here was part of my motivation for turning in my parking pass in March. My goal was to make riding the easy option, and now (finally) it seems like I made that goal. I have no trouble with the distance, my speed is good (at least good enough for me) and I have the packing/changing routine down cold. Partly it's experience, but partly it's gear.
One of my goals for this cycling season was to make biking an after thought; no need to think about it or dress for it. I have accordingly moved from traditional bike shorts to either knickers (rock climbing pants, specifically) or baggy nylon shorts over boxer briefs. This is a great combo, and for the distance of my commute more than adequate. In fact, I have dressed like this on longer rides with no... ill effects whatsoever. I also scored a pair of Keen SPD sandals this year, and that's been a very nice addition. Make the ride attire much more street friendly and the Keen's are the most comfortable bike specific shoes I've ever had.
We'll see what happens when the weather turns cold and days get short. I am generally afraid of riding Park/Portland in winter - the streets narrow and the speeds don't decrease, and the thought of getting hit from behind does not appeal to me at all. Chicago Ave. might be an option, but I am also a little concerned about the cold and the wet. One step at a time, though.