You can seal it but it s always going to be a weak spot.
Running wires through a roof.
Organizing roof wires into plastic flex tubing screwing to roof and sealing before it rains.
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.
Better to come out of wall then go up to the roof.
Rigid conduit with an outside diameter of 3 4 in and a fish tape long enough to reach through the buried pipe.
Please refer to these above options as a guide only.
To run the wires inside rigid conduit you ll need a hacksaw a pipe bender capable of bending 1 2 in.
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.
The best way is to go around the roof not through it.
Protect the wall with a thin piece of cardboard etc.
This option is quite self explanatory where a hole is simply drilled through the outer roof skin and wires passed through a rubber grommet into the roof cavity and fed down into the vehicle.
This is the least favorable option as it is not reversible.
Drilling through the roof.
Running wires inside rigid conduit.
And while loosely guiding the bit with one hand apply even pressure with the other holding the drill while running it.
As soon as you have a hole you are providing a path for water.
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.