10 times
There are: 495/9 = 55
6 of them with a remainder of 4
9 of them.
70 x 9 = 630
3 times with a remainder of 5
99 plus 9/9 = 100
(9*9)+(9+9)+(9/9) = 100
8, remainder 1
5
Nine of them
There are exactly 20 Nines. 9,19,29,39,49,59,69,79,89,90,91,92,93,94,95,96,97,98 which totals 18 and the last number 99 has 2 nines and therefore 20 nines in total.