Thanks for the hints. Seems like my Google Now works as expected then, but my lifestyle isn't (yet) supported...
The fact that it recommends I bicycle from Alcatraz is after informing it (through the icon with the three dots) I usually cycle, so that works right, sort of. My commute is bicycle+train, which unfortunately is not a combination of travel modes supported by Google Maps.
For me the "wand" displays 10 questions, which have a great deal of redundancy (5 out of the 10 are about the weather, for example.)
I wish it would pop up more cards by default that I could like/unlike, so it would learn more about my preferences over time.
To make sure Google Now is up to date you can pull to refresh. For me it's never more than 20-30 minutes out of date.