I removed my factory roof rack and used a couple of mounting holes from the factory nut serts. I have a power feed and two coax. I sized the gland nuts to match the existing holes that way "if" I ever wanted to remove them I just reinstall a nut sert.
Looking back I should have just cut a hole, used a 90 degree fitting and called it good.
In my profession, I have had to drill a whole bunch of holes in vehicles mostly for roof racks. I have a set of special hole saws just for that. If you use a drill bit with a stop (so it doesn't go deep), the bit will drill an oblong hole. Now you have sealing issues.
This isnt the brand I have but they look like this
Hole Saw
You can also drill then open it one size with a
Step Bit.
You need to make sure you have enough room to de burr the inside with any type of drill bit.