The Gray-Hoverman can offer the performance needed... (there's a lot of caveats implied in the "...") The work done by the author of this page is quite impressive,
http://clients.teksavvy.com/~nickm/gh_n_u_more_V.html
One fixed aim antenna can't provide a reliable solution that fulfills your 'want list'.
When looking at a 300' run, RG-11 comes to mind right away. You'll still need to carefully engineer the correct combination of preamplifier, (possibly) a line amplifier and a distribution amplifier.
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Is there a way to hook up two antennas with one pointed towards the Maine stations and the other pointed towards Boston/Manchester?
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Sure... But it can be expensive if you are going to try to reliably combine signals from the same bands (UHF in particular). Are you willing to consider building your own private cable TV head-end?
You could try passive filters from tinlee.com. Or, shift the incoming signal from an antenna to a channel that would be unique on your distribution system. Products such as the Holland HPH-860AD come to mind. You would need one for each real RF channel you wanted to insert onto your private system. With a price tag above $900 ea. this would be out of reach for most consumers.
If you are willing to compromise a little, there are other options...
http://forum.tvfool.com/showthread.php?t=820
http://forum.tvfool.com/showthread.php?t=2882
If I was in a situation similar to this, I'd start with two independently distributed antenna systems, both with an Antennas Direct DB8e + Antennacraft Y10713 + RCA TVPRAMP1R. I use HTPC technology and traditional TV sets, so the HomeWorx HW-150PVR (add a USB connected hard-drive and you have a PVR/DVR in addition to a the HD tuner) looks attractive as an axillary HD capable tuner for terminating a second antenna feed in a traditional TV set. (I might also consider using a CM-3410 at the antenna, particularly in the case of the H-VHF antenna with a fairly strong incoming real CH-11. That would require an enclosure to protect the 3410 from the weather.)