I can't tell you how many stories I know of people buying a house in a "really good school system" and realizing after a year that it wasn't going to work for their child.
Following up on Grinity's comment to this. We actually decided not to buy in the "really good school system", precisely because we thought we would feel obligated to use the schools there if we did, and we weren't at all convinced that they would be a good match for DS. Going through this decision made us realize that, although we do feel some allegiance to the public schools, it doesn't extend so far as to require us to choose them over some other option that is clearly better for DS.
That said, every choice will have its downsides; so for those so-inclined, second-guessing forever remains an option.
