I'm writing down notes for people so we have some vague idea of what each Outbreak character went through.
File #1:
"Outbreak" is set right at the start of the Raccoon City disaster, within hours of the initial attack on Birkin. This is the starting point for everyone in the game. Cindy and Mark both have canonical reasons to be here. IC, Kevin and David went through this.
"Below Freezing Point" is set in Birkin's lab at some point between the outbreak and the end of RE2, probably closer to the former. In-game, Yoko is always present; in-character, Yoko and David have both mentioned going through this area with George.
"The Hive" is set in the Raccoon Hospital, where George works. He is not always present, but it would make sense for him to be there.
"Hellfire" is set in the Apple Inn near J's Bar, early in the outbreak when the fire department is still active. There are no specific ties to any character in this scenario. Some fans think this is where Mark worked, but that's just a theory.
"Decisions, Decisions" is set at Raccoon University right before the bombing. George is always present; as such, while you can bring George to "End of the Road" in File #2, he couldn't've been there canonically. IC, Yoko has established that she went through DD with Kevin and Alyssa.
File #2:
"Wild Things" is set at the Raccoon Zoo, early enough in the outbreak that the RPD is still trying to evacuate people. Cindy is always present in-game, and Alyssa has a lot of reasons to be here (an exclusive file, lots of locked doors). IC, David and Kevin went through this.
"Flashback" takes up an entire day of the disaster, as a party bumbles around in the Raccoon Forest. It's probably pretty early on. Alyssa is always present canonically, and George has plenty of reasons to be with her (he's an experienced woodsman, you visit a hospital).
"Underbelly" is set in the subway station where Jim works, so he'll probably have been there. In-character, David was there.
"Desperate Times" is the infamous RPD scenario, which takes place in the east part of the building a few hours before Jill visits during RE3. This is Kevin's scenario, with a lot of bonus unlockables that only he can get. IC, Kevin was here.
"End of the Road" starts off in Umbrella's local headquarters, goes through the sewers, and ends in the same part of the city as "Outbreak" did. David is always here in-game; in-character, he has mentioned going through this with Mark and Jim.
So, right now:
Kevin: "Outbreak," "Wild Things," "Desperate Times," "Decisions, Decisions"
Yoko: "Below Freezing Point," "Decisions, Decisions"
David: "Outbreak," "Wild Things," "Below Freezing Point," "Underbelly," "End of the Road"
Unplayed Characters:
Alyssa: "Decisions, Decisions"
George: "Below Freezing Point," "Decisions, Decisions"
Cindy: "Wild Things"
Mark: "End of the Road"
Jim: "End of the Road"
There are a ton of expendable redshirts in Outbreak, like the unlockable characters, so if you wind up with a character who went through a scenario "solo," you could always make them the lone survivor of a group that otherwise consisted of redshirts.
Also, if you wanted to play an RE character but didn't want to play a canon one, there are a few possible survivors outside of the original eight and Linda, like Regan Morton (a single mom), Rita (a blonde uniformed police officer who survived the siege of the RPD), Austin, Patrick, Lloyd (all three are zookeepers), Samuel (a convict in the RPD cellblock), Harry (a cowardly police officer who quite resembles Michael Moore), or Rodriguez (a helicopter pilot and former Umbrella employee who was working with Linda to steal the Nyx).