Anything is possible when you use the right equipment. When I input your address with 30' of antenna height, the situation looks pretty grim; virtually no usable TV signals at all. When I raise the antenna to a height of 150' it appears that you have a number of stations available to you with decent signal strength. If the hill offers that kind of height advantage, then I would take advantage of the height that it provides: we can always overcome line losses with a good preamplifier. Almost all of the stations in your area are on UHF, so I suggest replacing your Radio Shack antenna and going with a high-gain UHF antenna like an
AntennasDirect DB8 or an XG-91. If you add a VHF yagi like a
Winegard YA-1713, you will probably see WBNG and WICZ from Binghamton, as well.
I would use a Hy-Gain AR40 Rotator, which will require some heavy-duty 5 conductor cable to carry the signal 500' probably some 16 or 14 gauge 3 and 2 conductor cable.
As for coax cable, you will need to spring for high-quality RG-11 quad-shield cable, which will have substantially lower losses on UHF than will RG-6u. I would use Belden 1525a RG-11 cable,which can be buried in the ground with no conduit if that is necessary.
If we figure 500' of cable, the nominal attenuation of the cable at 700 Mhz ( UHF channel 51) will be about 3.5 dB per 100'. If we multiply that by 5 (500' of cable), the total cable losses are 17.5 dB, which can be easily made up by a Channel Master Titan 7777 preamp. so we can cover your line losses and still have a little extra gain to spare to run 2 or 3 TV sets without an additional amplifier.
If you plan to mount an antenna on a hill, chances are that you will want to use some sort of a tower, and you can use a concrete based fixed tower like Rohn or a Taco tower, which will last more than 30 years with very little maintenance, How high you go is up to you, but the higher, the better, and I would use 30' above the crest of the hill as a starting point. If a concrete-base tower is too much for your budget, then you can ;ook at a telescoping mast from Channel Master or Wade, but you will have to guy-wire such an installation.
You can see that this is a BIG undertaking, and I don't know whether TV is worth it to you: the total cost of the tower, antenna, cable, preamp and other equipment can easily cost more than $1000.00. I would expect that you will see Elmira, Binghamton, and probably some of the Buffalo stations if you choose to go the route that I have described.