Curious as to how difficult it is for Boston guys to get to Springfield or Hartford. I have some friends in that area and wonder if it’s any good.

I used to do a lot of Boston - NYC travel. Hartford is about 1.5 - 1.75 hours from downtown Boston. If traveling to/from a suburb and not all the way to downtown Boston, you can knock 30-40 minutes off of that.  I don't do Springfield, but that's also a fairly easy 90 - 100 minute turnpike drive (tolls).  
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A couple of times, I stopped in Hartford to "stretch my legs" on the NYC - Boston drive. But those were for special occasions to see touring providers and it just worked out that our paths crossed more easily at Hartford than in NYC or Boston.  
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The downside for me (and maybe others): If the travel wasn't already on my schedule, I would NOT make the trip to Hartford to see someone I didn't know on the chance that it might be a good experience and that I wouldn't get stood up (NCNS or ghosted).  I mean, it's an additional 3 hours (round trip) minimum, gas/tolls/parking, ... it's just easier to stay in Boston.  
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Keep in mind that there is also a New England board (discussion and ads) for parts of NE that aren't Boston (Providence, Connecticut, Worcester, ...).  
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Good luck!