It sounds as if the trees will not be in the path toward the stations. Hopefully, the attic will not attenuate signals too badly, I would opt for roof mounting.
If you choose to attic mount, I would recommend you use the largest antenna that will fit in the space, while being aimed at 344° compass. Consider the Winegard HD7698P, which would not be excessive if mounted outside in the clear. If you split the signal to multiple sets, a preamplifier such as the Antennas Direct CPA-19 or Winegard HDP-269 would provide more than enough gain to overcome the cable and splitter losses.
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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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