Again I am not your Insurance company. I can tell you that with everything I know I could make life a Pain if I wanted to Not pay a Claim on your insurance if I was your insurance that is...
So if you wanted to do it right and have them not deny a claim I would look up some things on how to properly terminate Cat cable outdoors... What I will say is with that over a Power cord that is DC I would have an easier time denying a claim over that setup you showed then I would over a VERY thin Stranded wire running 5 or 12v to the camera...
To be honest I think your over thinking this a little... To me it is smarter to just Fire Proof the hole on the inside caulk the outside and call it a day..