[@Nightrunner] Was wondering if we could do something like in the comics where Dick indirectly meets a young Tim Drake the night his parents die since Tim is something of a fan. How that affects Tim down the line when he realizes that Dick is Robin could work pretty well with your idea I think. 

Edit @Batfamily ([@BlackSam3091], [@Blue Demon], [@Hillan], [@Nightrunner], and maybe [@Ruby] pending your design of Helena)

Here's what I've managed to compose of something of a timeline to keep us all coordinated.
~1981 - Bruce Wayne is born.

1990 - Barbara Gordon born.

1995 - Dick Grayson born

~1996 - Bruce begins training to be Batman

2009 - Bruce first hits Gotham as Batman but is unknown by the general populace and only is a myth among criminals.

2010 - Batman has become an Urban Legend among Gotham, Dick Grayson's parents are killed and he is taken as a ward by Bruce Wayne.

2011 - First Appearance of Robin.

2012 - Barbara Gordon graduates college becoming a member of the GCPD. The debut of Batgirl follows shortly afterwards.

2013 - Batgirl is reluctantly accepted by Batman. Robin (Dick Grayson) is also forcibly retired from the Robin role. Leading to him doing some soul searching and travelling the world.

2014 - Batman begins to train Jason Todd?

2015 - Barbara is attacked and crippled by the Joker. This tragedy brings Dick and Bruce closer together. 

2016 - Barbara becomes Oracle. Dick becomes Nightwing.


Batfamily Members:
Batman - Roughly Mid Thirties
Nightwing - 21
Oracle - 26
Jason Todd - 17? (Unsure as Hillan's skeleton isn't very clear and some of the timeline ideas significantly clash. Originally was stated to be younger however Sam has requested an older Todd.)
Tim Drake - 16? (Unsure, no sheet yet originally was stated to be 17 but Sam has requested that Tim and Jason's ages come closer in line with canon so Jason is older while Tim is younger.