Thank you for the replies yesterday about my drill. I think I’m going to get a cheap corded SDS drill and some big bits. This is what I need to feed through the wall and there is no way to detach the cable from the camera and feed it the other way. I know it needs to be weather shielded, but this is a mad amount of connectors!
That’s one way for sure. Downside is it more likely to result in mistakes and it’s a tedious PITA (source: done it dozens of times). Doing at the camera end on the PCB introduces the possibility of breaking something taking it apart or putting it back together. Plus, that’s a lot of wires to be messing with if one isn’t experienced. But it is a cleaner way of doing it than cutting the cables in half.
I think a rented hammer drill is the right answer. Simple. No chance of screwing the electronics. Can easily fill the hole again, if needed.