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If I were to put an antenna upstairs, I'm assuming one of the flat antennas installed in a window would be best?
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What would be best would be a small ALL_CHANNEL antenna because of your local channels 2 & 6. The small, flat antennas generally do very poorly on the lower channels although, at your distance and signal levels, you'd probably get away with it anyway.
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My FIL is constantly upset about the fact that the digital switch made all of this worse (it worked fine before he says).
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Yeah, that's what my grandfather used to say about the mule team on the farm, at least until he got a tractor and learned how to use it well. In the analog system, it usually took constant fiddling with the indoor antenna to get rid of snow and ghosting, but he's likely overlooked that. If you lived in a location that required those efforts with analog, digital reception will be "challenging", to say the least.