Um, OK. How about the fact that apartment listings in NYC are basically 95% spam, with brokers advertising apartments that don't exist, to pull a bait and switch when you call -- including on the specifically non-broker pages?
Searching by price is broken (look for $500 listings and it will return $500 daily, $500 weekly, $500 monthly, all mixed up together). Searching by neighborhood is broken, since it relies on keywords (which can vary, and are full of spam besides) instead of actual lat/lon.
I could probably write a book on everything that is broken, and that's just on the apartment stuff alone. (I understand it's better outside of NYC, but since NYC is the largest city in the US, that doesn't really matter.)