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Hi Chris, If you have a clear shot and you can point your antenna SSE, 177 degrees, you'll probably do just fine. Some of those stations to the north should come in as well. If you have any real interest in the lower channel numbers, 13 or less, you might need a dedicated VHF antenna but since most of the major networks from Boston appear to be UHF you should be fine.
About a preamp, more info about how your home is wired for coax would help. Add up the total length of the coax from antenna to your farthest TV. What kind of splitter are you using? Four way? Eight way? Hopefully not daisy chained from one location to the next to the next etc...
Assuming an eight way passive splitter is used and 100' coax run, there's at least 17 dB loss right there. With old coax and connectors, that number is higher still. With that kind of loss and the signal available at the antenna from most Boston stations, I'd go out on a limb and say you'd benefit from a preamp located at the antenna rather than a distribution amp.
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