WCYB might be possible from the bottom of the hill with a very long yagi antenna (or two stacked) cut for CH5 and aimed up. The CH5 antenna would need its own low-noise preamp; combine it with your WYMT antenna with a HLSJ.
http://www.hollandelectronics.com/ca...-Diplexers.pdf
WJHL is a lost cause from the bottom of the hill.
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I think an amplified repeater might do it though.
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Yes, it might, but that's not legal. The output of the preamp that feeds the second antenna aimed down to you would be an unlicensed transmitter. That is why one of the links I gave you, by GroundUrMast, suggested a WI-FI wireless connection.
http://forum.tvfool.com/showthread.php?t=1286
The way an amplified repeater works is this: the first antenna would receive the signal and be connected to the preamp input (which must be locally powered). Its output would feed the second antenna with vertical polarization to reduce interference from the original signal. The third antenna at the bottom of the hill also must have vertical polarization.
As I said, it's not legal, so I'm not suggesting it, but that's the way its done as described in some of the Google links for passive repeaters.
Passive means no amp.
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The problem, I think, is that the top of the hill is not LOS to my house, and VHF doesn't bend that well. Too many terrain features and trees. Would this present a real issue?
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VHF bends better than UHF, so it might work for WCYB.
There is such a thing as a legal wireless AV sender, but its range is limited, and you would need power at the transmitter:
http://www.bhphotovideo.com/c/produc..._Wireless.html
http://www.amazon.com/AVS-5811-5-8GH...2Fvideo+sender