I was wondering how could I drill a hole directly through my first story ceiling to the second story floor without severely damaging neither floor nor ceiling. If possible, could someone give me detailed advice on what to watch out for and how I would drill it?
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I have never done this, but this is how I would do it:
First be sure there is no reason to suspect that wiring or plumbing is obstructing the space you want to run the wire through.
Then drill through from one side just into the interior space so if any thing important is there, you won't drill into it. Electricians often use long, flexible drill bits to drill through ceilings and top plates.
Then use a probe (e.g., piece of coat hanger wire or small diameter wooden dowel) to feel in the space for obstructions (better yet use a borescope to visually examine the space).
Work a long drill into the hole you have made until it hits the opposite wall and only then turn on the drill. After this drill goes through the other wall you can use it to pull the wire through, simplifying the task of linking up the two holes. Or go to the other side of the wall and drill exactly where you want the hole and stop immediately after you penetrate into the interior. Use a probe to link up the two holes.
From one side or the other you might have to drill a 2" or so diameter hole to be able to get the wire through. You would then have to plug this hole except where the small wire goes through. I would use a hole saw on a drill. The piece removed by the hole saw could be the basis for a plug.