[HockeyIlliterate]

[Trying to quote llwhiteoutll, but their post isn't showing up in my reply box]

Regarding drilling the hole, I thought that the way to do it was to drill from the inside out, using a very thin drillbit, which will mark the center-point of your hole's diameter.

You then go outside of your house, and using a hole cutting bit, drill from the outside in, placing the center-point in the hole that you had previously drilled when you were inside of the house.

That way, you know where your hole is going, that it isn't going to damage anything inside the house as a result of accidently drilling too high/low/left/right/etc, and your outside-facing cladding isn't destroyed by the bit.

ETA: FlamesKickAss said the same thing, but used less words and posted it quicker than I did.