This is a little trickier than usual - we're doing things in one time period, but aiming for a plot payoff in another - so it seems like a good candidate to toss lots of ideas into one thread and try to match them up. So here's a start:
Randall: Starts working at the pawn shop, then the crazy former owner dies and leaves him in charge.
George: Gets elected, hires the present-day members of Special Projects, is a jerk to Sierra on at least one occasion. Significant time in Washington DC, if you want your PC to have been there.
Matt: No idea! Maybe investigating Daphne's thefts. Any hooks involving Janice would also be cool.
Carl: Somewhere overseas working for the CIA, if you want your PC to have been there.