ok well sadly the worst thing i can say about shady side is that it's overpriced and hard to park.
it's an upscale community, very historic and nearest to the south side of the city. (i live north) it's mostly Yuppies and "Adult alternitive" if you know what I mean wink wink.
most kids go to shady side academy. Closest competive football team is Central Catholic (in oakland) lot of pretty houses but no yards.I moved here after high school so i'm not in the know of all the dirt.