Born and raised in the heights, just off white oak and studewood, although it wasn't nearly as trendy back in the 90's when i lived there. Jimmy's ice house used to be a cool hole in the wall back in the day, atmosphere has changed drastically though. Andy's cafe on 11th, across the street from Hogg. They just added cafe to the name to appeal to all the hippies that began moving in, it actually a mexican joint. Most of the menu is pretty average, but get the beef burritos with cheese, you can thank me later.
They go past 20th as well, they pretty much took over Northwest Heights. You check out the housing from google maps. The area is drastically changing, looks nice.
Lots of good places listed already. Love Downhouse and D&T for beer, Boomtown and Waldo's for coffee. For restaurants, I would also add Zelko Bistro and Shade.