Yes, painting is a pain !
For me, painting the hole is the best. . And the best "paint" is actually "Glass Marker" made by Rustoleum. . It dries fairly quickly and I can sometimes glue in the brass tube within about 30 minutes. . The "paint" is a bit fragile, though, so you have to be careful not to scratch it when pushing in the tube. . If you have a large selection of drill bits, it is best to make the hole size about 0.003" bigger than the recommended drill size to allow for the paint thickness. . Also, there is not a wide color selection, so you might have to mix to get a better color match for what you want.
I use a Q-tip to apply the paint to the inside of the hole.
Sorry, I don't have any pics to show.