Well...I'd hate to throw my opinions on the High Schools...
I graduated awhile ago from Whippany Park (Whippany). Pretty good school. I lived before that in East Hanover. Both had good schools, but I would say Whippany's was better.
I knew a lot of people from Chatham, 99% of the graduates there are the kind of snobs most people want to hit in the face. Education wise, it's a great school. I don't think the environment there breeds good character. My opinion.
You may want to look at surrounding towns. Or not. If you're looking in the general area of Chatham, make sure you stay in Morris County. We pay 1/2 (or even less than 1/2!) in property taxes than they do in Essex. Car insurance is also much less.
Also, look into the differences between Chatham Borough and Chatham Township. They're mostly refered to as one. Weird things, like on one side of town you can throw out as much trash as you want. On the other you can only throw out a certain amount of bags of a certain size a week.
It's a beautiful area. We're close to the city, plenty of parks, good schools, low crime, lots of highways. If you move into Summit/Chatham/Madison/New Providence you have train stations that go directly into NYC.
-steve in nj-