The article on the "hitchhiker's paradox" that this links to made this much more clear to me (as well as being shorter): https://the8layers.com/2016/10/30/how-long-will-you-wait-hit...
On average, wind reduces your groundspeed. The short of it is you spend more time in a headwind, so you spend more time experiencing the bad than good.
There's also the fact that even a direct crosswind slows down you ground speed (you lose some speed for correcting your course) but I don't think this compares to block chains or hitchhikers.
Imagine an airplane that flies 100mph. You want to fly north, but you have a 90pmh crosswind from the east. You have to point almost directly into the wind just to keep from getting blown off course. You can turn a little to the north, and you'll go very slowly. If you instead have the wind come from the east, you still have the same problem.
Maybe easier analogy: to get directly across a river, would you rather swim across one going fast or slow?
However, if the wind doesn't shift you are now taking even longer to get there because you'll have to turn to go straight upwind once your destination is directly upwind from you.
An interesting related fact is that with equal distance traveled through headwinds and tailwinds a slower plane will be relatively more affected. From ~12% longer time with a wind speed 1/3rd plane speed down to ~1% with a wind speed 1/10th plane speed.
Only if you didn't have to do the standard physics problem comparing swimming X meters upstream and back downstream to swimming X meters across and then back across.
You will, on average, wait 10 minutes. If you hitch hiked that road 1000 times, you'll have waited 10 minutes on average.
But that doesn't mean you won't wait longer that 10 minutes on a given wait. In theory, you're waiting time will follow an exponential distribution, so you could wait 1, 10, 50, or even 1000 minutes (although quite unlikely)!
But again... On average, you'll be waiting for 10 minutes from car to car.