I have lived in NY, the Bay Area, and the Boston area (both Cambridge and the suburbs). I am in London/Frankfurt about one week a month and spend time in Toronto, Calgary, and other places (we have a cottage on a lake outside of Montreal). What I love about Boston: there are more interesting people per capita than in any other city I have lived in or visited (doesn't apply for folks in fine arts or music). We meet interesting academics (from Harvard, MIT, Tufts, BU, BC, ...), interesting consultants (from BCG, lots of independent firms), biotech folks, investment folks (PE, VC, equities/bonds, hedge funds), artists, architects, psychologists/psychiatrists. Lots of interesting people. This is potentially relevant to you.

The kids of the folks will tend to be bright and motivated and a number of the public schools are quite strong. Plus, there are lots of good private schools. In an ideal world, your kids' worldviews are expanded by having classmates and friends from interesting families. Where does this happen? Cambridge for sure, but housing prices are pretty extraordinary there. Towns with good schools include those in the Western suburbs (Lexington, Lincoln, Concord, Acton, Weston, Newton, Wellesley, Harvard, Bedford, Belmont, Dover-Sherborn, Wayland), those more urban (Brookline for sure, Cambridge maybe), and those South of Boston (Sharon, Hingham) and others (Winchester). The following article shows a graph of how the school district performs (how many years the students in a town are above or below the national average) and income. http://www.nytimes.com/interactive/2...ares.html?_r=0. Notice that a significant percentage of the schools in the upper right hand corner are in Massachusetts. Houses in most of these towns are reasonably expensive to very expensive.

I don't know how to evaluate these ranking but here are a couple (http://www.bostonmagazine.com/best-s...-high-schools/, https://k12.niche.com/rankings/publi...massachusetts/).

As PVDtoDEL suggests, live in a less expensive town if you send your kids to private school, but it could be as he/she suggests, live in less expensive place, possibly next to a more expensive place.

Also, you need to think about whether you are going to commute by subway, care or commuter rail.