There are no magic antennas that can "see" through trees. Trees do serious damage to TV signals. Fortunately for you, VHF signals get through a little better.
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Will it just require an antenna with more gain?
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That isn't usually the solution. You have to try different locations and higher if possible.
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I just don't want to do it twice.
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I understand, but there is no way I can give you a guarantee. You and your son will need to do some testing.