I put one or two drops of oil into the tool I am going to use. Then I hook the air up and run it a little bit. I then wipe any oil that came out and get to work. I do not use my air tools that often so I only oil the tool I am going to use right before I use it.
Most air tools will tell you (instructions or stamped near the air inlet) to oil daily with 1-2 drops.
I use the Marvel air tool oil, I love them smell of it too