Hello Peter....You should be asking yourself where in "Greater Boston" do you want to live. Do you want to be in a Boston neighborhood, i.e. Charlestown, Southie, JP, West Roxbury, etc.?
If you don't want Boston, but still want to have that "city" feel, Cambridge or Somerville might be a better fit.
If you want the Greater Boston suburbs, there are a lot of options as well.
The Newton/Wellesley area offers great proximity to Boston, superb school systems, and strong communities. The price of condo's & townhouses will reflect this in this much sought after area.
Boston's South Shore communities such as Weymouth, Quincy, & Milton are all nice communities too. There might be more bang for your buck in a condo or townhouse in this area. Keep in mind your commute to the city as well. Drive traffic on the SE Expressway is always tough, however the MBTA train and commuter boat shuttle to downtown Boston is a nice option.
North of Boston is close and convenient as well. Communities such as Melrose, Reading, Wakefield and Stoneham all offer close proximity to Boston, good school systems, and a strong re-sale market, especially with condo's & townhouses, which seem to be holding their value even in a downward market.
Wherever you decide to buy, it has to make sense to you and your family (and your future family!). The internet is a great tool for this. You can check out schools, crime rates, median household incomes, and any number of criteria you'd be interested in while checking out possible towns to buy in.
It really is a great time to buy due to low interest rates and a high inventory of properties. Enjoy the process and best of luck to you in your search!