Better to come out of wall then go up to the roof.
Running wires through a roof.
Running wires inside rigid conduit.
Rigid conduit with an outside diameter of 3 4 in and a fish tape long enough to reach through the buried pipe.
You can seal it but it s always going to be a weak spot.
Protect the wall with a thin piece of cardboard etc.
I did a painstaking process of trying to wire up a new power panel in our rv.
If the sites that you want to run wire to are on the outside of the house you should not need to drill a new hole.
Organizing roof wires into plastic flex tubing screwing to roof and sealing before it rains.
Be sure to check out the latest gear i use on my adventures.
The best way is to go around the roof not through it.
As soon as you have a hole you are providing a path for water.
When cutting through drywall from the interior of a room use a utility knife and cut carefully you don t want to drill through a hidden wire or the paper backing of the attic insulation.
To run the wires inside rigid conduit you ll need a hacksaw a pipe bender capable of bending 1 2 in.
Additionally if you ever need to redo the roof it will be a pain to deal with the wires that are now in the way.
Drilling through the roof.
Please refer to these above options as a guide only.
This is the least favorable option as it is not reversible.