If anything, it seems like the yuppies and hipsters are pushing deeper into Uptown and Rogers Park, which is/was the Northside's "hood zone". They aren't leaving.

I haven't kept up with the goings on at Chicago Public Schools in years, but Walt Disney was always considered a good school for kids. But this was years ago, don't know what it's like now.

The Latin School of Chicago is a good school, too. Private school.

The place that replaced La Pasadita, Authentaco, beats the breaks offa La Pas; handmade tortillas made inhouse, just an all-around better taqueria.

And quiet as kept, Birria Huentitan was always better than La Pasadita, for burritos anyway.

You should also consider Oak Park, Il. Kinda like Chicago's version of Columbia, Md or Berkeley, Ca (kinda sorta). Multiethnic, liberal, and progressive.