Most of the time. We live in NYC and have gotten anywhere from 0.5 mile to 3.5 miles range here, depending what part of the city you're in. There's nearly no such thing as LOS in a city unless, say, you're in a skyscraper ;)
Ah, I'm just surprised that buildings ended up mattering when you were deciding between 150MHz or 900MHz.
While people like to complain about the frequency getting higher and propagation dropping off (especially related to 2.4GHz and 5GHz wifi), I haven't found a good paper that guarantees that's the case. Anecdotally, I can receive a 5GHz signal in my office in Manhattan from a radar in Floyd Bennett Field, 12 miles away, with buildings in the way. Similarly, inside my apartment, I have much better luck with 440MHz radio communication than 144MHz communication. (Ground floor, so not that great either way.)
Being limited to 4W EIRP in the 900MHz ISM band probably played more of a role?
