No Attic/Crawlspace/Basement Installation?

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?
 
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?

Try Freight Harbor - they have some longer 8" masonry bits you can use.. better for hammer drills, however I got one to work with my larger drill well enough for the few holes I needed to make.
 
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?
I think I'd generally drill a smaller hole and use a junction box.

I have a big ass roto-hammer sds+ drill that can pop 1 1/4" holes in solid rock/concrete. But that wouldn't work so well on stucco with the metal lathe and OSB behind.
 
I think I'd generally drill a smaller hole and use a junction box.

I have a big ass roto-hammer sds+ drill that can pop 1 1/4" holes in solid rock/concrete. But that wouldn't work so well on stucco with the metal lathe and OSB behind.

For locations where I have attic access behind the camera, I do plan on using a junction box and only drilling a hole big enough for the un-terminated cable.

For other locations, I still plan on using a junction box behind the camera to protect the pigtail, but the cat5 will need to travel some distance before going through the wall into the attic. If that run is within a conduit, then I'd have a conduit body with a hole facing the wall. So the cable inside the conduit needs to enter the attic at that point. Instead of putting a hole in the wall big enough for a piece of 1/2 - 3/4" conduit, I wonder if I could just clamp the conduit body down tightly against the outside wall and drill a small hole through the wall for the cable. Then of course caulk well around the hole to prevent water getting in.

BTW, the stucco just has chicken wire and paper behind it. The house is 50 years old.
 
For locations where I have attic access behind the camera, I do plan on using a junction box and only drilling a hole big enough for the un-terminated cable.

For other locations, I still plan on using a junction box behind the camera to protect the pigtail, but the cat5 will need to travel some distance before going through the wall into the attic. If that run is within a conduit, then I'd have a conduit body with a hole facing the wall. So the cable inside the conduit needs to enter the attic at that point. Instead of putting a hole in the wall big enough for a piece of 1/2 - 3/4" conduit, I wonder if I could just clamp the conduit body down tightly against the outside wall and drill a small hole through the wall for the cable. Then of course caulk well around the hole to prevent water getting in.

BTW, the stucco just has chicken wire and paper behind it. The house is 50 years old.
either approach would work. you could even pop it straight into the attic via the soffit.