You are a cab driver who pools passengers. You pick 3 people from a destination and drop 1 after an hour. 2 people climb aboard at the same time and you drop 3 at the next destination. After some time, you pick 2 passengers only to drop 1 after a short distance where 3 more passengers climb up the cab. You leave the rest of the passengers one by one to their destination and then come back home.
A new Engineering building containing 100 offices had just been completed. John was hired to paint the numbers 1 to 100 on the doors. How many times will John have to paint the number nine (9)?