Last night I typed in "Hollywood" while trying to find a map in Los Angeles, and of course Apple Maps took me to Hollywood, FL instead by default.
Is that a first-world problem? Absolutely. But it's little quirks like that which still make it feel like a completely counter-intuitive app. So I hope it does continue to improve.
Edit: I also gave Apple Maps a try while vacationing in San Francisco. I typed in "Golden Gate Bridge" and it gave me directions to a diner. C'mon Apple. You prominently show the GGB in the background of your page for CarPlay, yet can't even take people to it when they type it in?
I was curious whether what you said was true or not. So I opened up Apple Maps on my Macbook Pro to try it out. I live in Portland, OR so that's where Maps opened up first.
I first typed "golden gate bridge", it immediately dropped a pin dead center on the Golden Gate Bridge in SF.
I then type "hollywood", and showed dozens of pins of places in SF with Hollywood in its name, that included a cafe, a bakery/restaurant, a launderette, a market and deli, dog groomer, video stores, and Frederick's (of Hollywood). I considered that fair since my map was in SF when I entered the search.
So then I entered "hollywood, ca" which then took me to the Hollywood neighborhood in San Leandro, CA (East Bay Area). We happen to have a Hollywood District in Portland as well, so I tested it by going back to Portland, and re-entering "hollywood". Sure enough, it dropped a pin into the middle of the Hollywood District of Portland. Which makes sense. If I live in Portland and type in "hollywood", it is far more likely that I am looking for the local Hollywood, not the one in LA.
Next, I entered "los angeles", which takes you where you expect. Then entered "hollywood", which dropped a pin on the Hollywood Hills. Pretty good. Then I entered "hollywood sign" which dropped a pin right on the Hollywood Sign with an address: 4014–4030 Mount Lee Dr, Los Angeles, CA 90068.
For the final test, I went back to Portland, and entered "hollywood sign los angeles". It went all the way back to the right place in LA.
Don't know why you ran into an issue or *when* this was an issue, but it seems to be working exactly as it should for me. Perhaps you should have verified your own easily testable issue before declaring it doesn't work. It took me less than a minute. So expect a lot of well-deserved flack.