Mr_D
Getting comfortable
Post a couple of pics of the outside of your house, we may have some ideas that avoids the roof.
On the outside, use a this: Carlon 3/4 in. PVC Type LB Conduit Body-E986E-CTN - The Home Depot
Cut the hole with the proper sized bit, so the end of the LB fit's snuggly. Use a short piece of 3/4" conduit through the wall.
Caulk around where the LB enters the wall, then use expanding foam to seal around the wires entering the house.
My house is stucco. What do you use to drill a ~1 1/4" hole through it? All my masonry bits top out at 1/2" and all my bigger stuff (hole saws, spade bits) are for softer material. Did you get a big, expensive masonry bit or just sacrifice some regular bits?