Ok, so guys I think I have figured out the mystery of the TD timeline, basically here's how it goes:
TDI: Takes place in Summer 2008, the original generation is 16
TDA: Takes place two days after the TDI special, original generation is stil 16
TDWT: Takes place in Winter 2009, seeing as Cody has his 18th birthday in Awww Drumheller!
TDROTI: Takes place in Summer 2010, Chris is a rich man, it is possible that it wasn't that very hard for him to buy the island back, or he bribed the people who took care of it while he was away.
TDAS: Summer 2011, proven by the fact that Chris was in prison for a year, and that Alejandro said he was stuck in a suit for that length of time.
TDPI: Fall/Winter 2011, depending on how much time it took for Chris to get a new island. Fall is more plausible due to the lack of any natural snow, but winter is more realistic.
RR: Early 2012, January or Feburaryish, Leonard is still 16, so it has to place soon after PI. Plus, unless they all have early birthdays, it still fits Owen, Noah, and Geoff's age of 19 during the show.
I believe that this may or may not be the solution to the mystery. Leave your thoughts in the comments below pls.