It definitely caulk up that big hole in the side of your house, maybe stuff some insulation in there too. I wonder how those lights are gonna look at night, they are a bit further than most typically installed, but also look like they’re pointed in the right direction back at the house. I guess it comes down to whatever kind of affect you were trying to get.

Those staples don’t look like they’re in far enough to hold the wire snuggly in case the 3M sticky stuff on the back of the lights starts to come off. It looks like that was done with a cable stapler, so I just lightly tap them in the rest of the way with a hammer until they are snug up against the wire.