Could be epic. I think it would need to span multiple games as so much happens during those time frames.
In jail you could have a risk reward type system where you could snitch, but use the information to continue dirty work ala Whitey Bulger. Climbing rank could work in a meta game type system after the main story is complete as to allow a narrative to still exist in the world for the main story, but to give a end game system for those who simply want to continue.
Speaking of 1983, they could have an entire cocaine cowboys type Mafia in Miami. Everyone had their hands in that cookie jar lol, Cubans, Colombians, Mexican Mafia, Italian Mob, Haitians etc