It will be next to impossible to drill downward under the portion of the roof that slopes to the attic floor without a right angle drill.
How to run wire down wall from attic.
To run cables vertically go into the attic or basement and drill holes in the wall plates above or below the locations of connection boxes.
If you will need to fish wiring through a wall drill a hole through the wood plate in the attic only.
And use semi rigid wiring fish tape to pull your wiring down to your outlet location.
Run the wire or cable to its destination.
Return to the attic or basement and drill through the wall plate where you want to guide the wire through.
When you re installing a new electrical circuit or running speaker cables in your home you have to run the wires inside your finished walls.
Attach the wire or cable to a fish tape or coat hanger using electrical tape and feed it into the hole until it reaches the opening at the other end.
Cut a hole for each box with a drywall saw or a saw appropriate for the wall material then feed the wires down from the attic or up from the basement toward each hole using a fish tape or a fish stick.
When adding or replacing wiring in finished walls most electricians will attempt to make the horizontal portion of the cable run in the unfinished attic or basement crawlspace areas looping the cable down or up through the wall cavity across the floor or ceiling joists then vertically through another stud cavity to the next wall box opening.
If you re working from the attic you can drop a weighted string down wall cavity then attach the wire to the string and pull it through.
You may encounter nails so choose an auger drill bit which won t get damaged by metal.
If you re working in a crawlspace you can use a flex bit drill to drill this hole from several feet away.
When working from an attic space it will be significantly easier to access a wall space on the floor below by working either an interior wall or the exterior wall that is on the gable end of the structure.