I'm leaving this for reference for any fanfiction I make or post I make. Take it or leave it. Do what you want. I'm just trying to get all of Bruce's Robins in order and some of the DC timeline.
Bruce Wayne leaves at 17 after graduating high school early
Bruce graduates college at 19 with a business degree (Alfred didn’t order him to, but he strongly inclined Bruce to do it)
Bruce trains until he is 22
Bruce Wayne returns to Gotham and becomes Batman at 22
When he is 23 (AKA Year 2) The Long Halloween scandal occurs
By the end of Year 2 Harvey Dent is officially Two-Face
At the beginning of Year 3 Bruce adopts Dick Grayson
During the middle of Year 3, Batman meets Superman for the first time. After an adventure, they become friends
At the end of Year 3 Dick Grayson is properly trained to be Robin
By Year 4, Bruce is officially stuck in a month long entanglement with the Al Ghuls. Bruce and Talia sleep together multiple times throughout this month. By the end of it, Bruce has cut ties with the entire family and they will occasionally feud.
By year 5, the Justice League is formed
During Year 13 of Bruce’s career, Dick turns 18 and has a falling out with Bruce. Dick leaves to become Nightwing and form the Teen Titans
Ages to keep in mind so far
As of Year 3:
Bruce Wayne is 24
Dick Grayson is 8
Barbra Gordon is 9
As of Year 13:
Bruce Wayne is 34
Dick Grayson is 18
Barbra Gordon is 19
(Barb starts doing Batgirl stuff after 6 months Dick becomes Robin and becomes recognized as a Batfamily member by the end of Year 4)
During the middle of Year 13, Barry Allen dies during Crisis. The Crisis doesn't matter, but now Barry Allen is dead due to stopping a world ending event. Wally West is now The Flash
Year 14, Bruce finds Jason Todd stealing his tires on the anniversary of his parents death. This cracks him up so much that he adopts him (that’s actually canon)
By the middle of Year 14, Jason Todd has been trained to become Robin
By the beginning of Year 16, Joker kills Jason Todd
Ages so far Year 16:
Bruce Wayne is 37
Dick Grayson is 21
Barbra Gordon is 22
Jason Todd is 16
Jason Todd is revived by the League of Assassins before he is buried. Bruce Wayne is too frazzled to notice the fake body
Shortly after the death of Jason Todd, Joker shoots Barbra Gordon in the spine, causing her to be paralyzed from the waist down. Since Batman didn’t have a Robin, Batman almost killed the Joker
By the middle of Year 16, Tim Drake recognizes that Bruce is a hop skip and a jump away from killing someone and forces himself into the Batfamily. By the end of Year 16, Tim Drake is officially Robin
Year 19: Jason Todd officially debuts as the Red Hood
By year 22, Damian Wayne is in the picture and Tim Drake becomes Red Robin
By year 24, Jason is accepted back into the Bat Family as he vows not to kill anyone ever again
By year 24 (basically current day):
Bruce Wayne: 45
Dick Grayson: 29
Barbra Gordon: 30
Jason Todd: 24
Tim Drake: 18
Damian Wayne: 14
Got any additions? I'd love to hear!