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There's a pretty simple tool (available at most any home improvement store) that allows you to remove one piece of siding by sliding under the joint and hooking around it so that you can unjoin the pieces and then rejoin them later. I'd just fish the 2nd wire under the siding and then remove the piece that needs to be removed in order to drill the hole and route it into the house. Tape things up nicely so that you don't get a buldge under the siding, and put the piece of siding back when you're done.
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I like to shop at Sadoun Satellite Sales
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