At my last job next to the Caltrain station in Palo Alto, it took me about an hour on a good day. The pain points are always:
1) getting onto 237 portion of the freeway since there are only 2 lanes from Milpitas.
2) merging onto 101 N from 237 W
3) Where 85 N Meets 101 N, it backs up at least a mile, sometimes through to Ellis.
4) If there's an accident anywhere from Redwood City to Milpitas, there could be an extra 15 minutes for a fender bender to an extra 45 minutes if multiple lanes are closed for cleanup.
The other two solutions are:
A) 880 N from Milpitas to Dumbarton is no picnic either.
B) 237 to El Camino and roll up that way
Neither of which give any advantage.