Guess no one's ever done any UHF weak signal work...
I give up - WAAAY too much involved! Thanks for all the great input though.
DON'T GIVE UP!
Here's the deal - I used to be able to hear Barnstable County ("Cape Cod") very reliably when I was in NJ and they were on VHF. They were on the same channel as one of the local police departments, so I couldn't help it on my old Bearcat 210. It was not an everyday occurrence but I didn't have to put up a thousand foot tower or fly lots of aluminum to do it.
There are certain conditions that allow you to hear it, and, much of the path is along the Long Island Sound from you, so there is a VERY GOOD CHANCE you will hear them several times a year, especially in spring and fall when the days are warm and evenings are cool or still cold.
Get an 800 yagi antenna. There are a lot of them around at hamfests or on auction sites, or even in the garbage from time to time. Does not have to be fancy.
Get some good coaxial cable that does not have a long run. Something like 25 feet of LMR400 should be fine. If you find a scrap of 1/2" or 7/8" hard-line with the connectors, that's better. It's not hard to find.
Point your antenna 68 degrees. That's about East-Northeast.
Program the system(s) in. Let your scanner go.
Under the right conditions, and if you're not overwhelmed by noise or other co-channel stations, you WILL hear them. Like I said, not every day, but it probably will work several times a year. It's not impossible.
Here's a not too bad explanation of the theory of why this is possible. It is not the same mechanism as low band skip. Something like it, but this is atmospheric, not solar-terrestrial.
Remember, you are NOT relying on line of sight in this mode - none of the previous discussions about line of sight propagation are relevant! I've moved a few times since my NJ days, but I am near the ocean again. It's not uncommon for me to hear (and talk to) stations 300 miles over water on UHF with a modest yagi up about 35 feet and much less effective radiated power than they would be running.