Drilling holes through structural members shouldnt be a problem, as you'll need a small hole only for coax. Make sure to center your holes as much as possible on wall studs, and make sure to stay at least 1 1/2" from the edge of any joist you need to pass through.
And distribution amplifier is what I was thinking earlier, but forgot to put in my post at all. One of those should do the trick for you for any signal loss problems.
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