You may want to consider other paths. I commute from SE Stark & 111th (not too far from Powell & I-205) to the Barbur Blvd. transit center, then a bus out to Wilsonville. The best route for me wound up being just blasting down Division, cross over the Hawthorne bridge, then up Barbur Blvd. If he's open to multi-modal transit, then that might be a winner.
Another possibility would be the Springwater Corridor, across the Sellwood bridge, then somehow over to Tualatin.
I'm not saying my route is best, just suggesting to consider other routes. It took me the longest time to realize that just because I drive a certain route, doesn't mean I need to ride that same route. Once I had that epiphany I took another look at the map and started riding my bike (most of the way) to work taking a path that was basically perpendicular to my driving route.