I've been thinking about how to phrase this question for sometime so I think it's time to take a stab at it.
Let's say a kid is accepted to two schools -- one quite rigorous, one less so.
Do you encourage this kid to choose the school that is known for its rigor, even though you feel it could be pushing the boundaries of kid's intellectual and stress capacity?
Do you encourage kid to select the one that is considered a good school but more relaxed than first school academically? At this school, kid would probably be able to participate and socialize quite a bit more than 1st school, and you know the kid could handle it academically.