Kanto and Hoenn -[Three years]-> Johto and Sinnoh -[At least three years, almost certainly more]-> BW -[Two years]-> BW2
Kalos takes place at roughly the same time as BW2, as confirmed by the recent timeline and implied by in-game content.
We know it's been at least eight years since the end of FR/LG since Blue at some point before X/Y studied abroad in Kalos, so he (and Red) are at least university age.
>>19181033Event Pokémon are canon, the player character catching them is not. Red's six Pokémon are the only canon catches by a player character, discounting the obvious pick of one of the starters.
We also know that several unique Pokémon in the games were not captured by the player character, like Mewtwo who was not captured by Red or Gold/Ethan as it's available in Kalos.
>>19181268The characters all look the same because the PWT isn't canon and/or GF didn't feel like wasting a few weeks of development time coming up with appropriately aged new designs for over fifty characters.
Even ignoring the original BW there's over five years of time between Gen I/III and BW2. Tate & Liza and Maylene are still kids. Red and Blue are adults but look the same as when they were thirteen in HG/SS.
The only reasonable option is to say either the whole event or the character's appearances aren't canon.
As for the gap between DPPt and BW, I think a fair estimate would be about six years. One year for LRG to return home, fall in love and have a kid, five years for the kid to grow up.