He was complaining that Apple didn't select a FAMOUS neighborhood 2000 miles away over a medium-sized city 900 miles away. I agree with you that proximity and recent search context matter; it is a map application after all, not an encyclopedia. The OR was complaining it should weight fame over proximity, as an encyclopedia should.
Actually, it sounded like he was in Los Angeles when he tried to find Hollywood on the map. Likewise, he was in San Francisco looking for the Golden Gate Bridge and was pointed to a diner with the same name (that error I can sorta understand).
However, if I were to type in Applebee's (just an example - I wouldn't actually eat at an Applebee's