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!
For a similar project, I got this doofy hole saw set from Harbor Freight:
https://www.harborfreight.com/1-14-in-3-14-in-carbide-grit-hole-saw-assorted-set-9-piece-57708.html
I was able to knock a hole large enough to shove a piece of 1-1/2" PVC conduit through a foundation wall without much trouble, using a regular (non-hammer) drill. It took about five minutes, no sweat. Although obviously I had to come at it from both sides. I later did the same to put a length of flexible conduit through to power my mini-split outdoor unit.
If I were you I’d use the smallest saw in that and then use one of these conduit junction dinguses on the outside to house the plugs and ensure they remain dry – and enable you to access them if you ever need to fuck with it later.