More than doable within 10-20 miles.. You may want to live in a town close to a public transport hub if you plan on working in Boston, way easier than driving into the city if you have a normal 9-5 M-F job. In my experience, I've never been in a town in Massachusetts that you would need bars on the windows (besides some areas of the cities, of course). And maybe Brockton. Certain towns are way more expensive than others. I have trouble with dog sports here. No lure coursing (maybe...one or two AKC events a year, between MA and CT). I looked at IPO clubs, there are not many at all, I believe there is one around Boston that always says "Membership Full". There are plenty of agility/rally/obedience training places around (compO is becoming more phased out, from what I've seen). Dock diving competitions are frequent in the summer, but there are no training clubs in Massachusetts. Probably the closest is Seacoast Dock Dogs in Maine. I've only seen Barn Hunt events in CT. Right now I live closer to Springfield, but I have lived in Middlesex County-Douglas, Hopkinton, Framingham area. Let me know if you have any more questions!