If I were in your situation, reliable reception of the Pittsburgh stations would be my goal. To do that, I'd use a Winegard HD7698P and Antennas Direct CPA-19 preamp. The preamp will easily provide the gain needed to drive a 100' coax run.
Unfortunately, that's a large antenna which is more than I would trust to an unbraced J-pole. Stronger tripod or eave bracket mounts would be my choice.
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If the well is dry and you don't see rain on the horizon, you'll need to dig the hole deeper. (If the antenna can't get the job done, an amp won't fix it.)
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