Just an update. I went to the cabin this weekend fully expecting to have to replace the long cable run with a better quality cable (RG-6 currently) but thought I would try the amplifier first. Picked up a $20 amplifier from Best Buy enroute and once installed, all issues resolved. Signal didn't hesitate once and I got every single channel at the guest trailer that the cabin got all weekend. We had the TV set up outside at the trailer for the World Cup which was great.
Cheap and easy fix. Thanks everyone.
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