Got a stupid question. I don't know much about CV but I did look up the plot (and I'll likely be watching a walkthrough now of the original since I wanna know about it since we're getting a remake) but it looks like it takes place 3 months after the raccoon city incident and that Claire had Leon message Chris about her whereabouts. When did Leon get access to a laptop? Or Internet and his email? Was this before he was captured by the govt? Actually when did he and Claire swap emails, presumably before she left to go look for Chris?
(also pffft Chris being a slob. I need to know what his and Leon's apartment/house looks like after they move in together.)
Leon's Treasonous Emails, as I like to call them, are something I feel may be developed further in this remake. Previously, none of this was ever shown on screen, we just learn it from dialog in the game and the files, but apart from Claire ending up at Rockfort while trying to find Chris in December of 1998, we've never really known the exact timeline of things.
Based on how things shake out/what we know of the existing lore, Claire and Leon likely exchanged emails shortly before Claire split off from Sherry & Leon to go find Chris. I see this oftentimes get misconstrued as her like ditching them in the middle of the night or something, but its important to note that this was a mutual decision. Leon told Claire that he's got things covered with Sherry and that she should go find Chris, so he knew what she was doing.
We don't know the exact timeline of what happened to Leon and Sherry, but based on the picture of Leon that Krauser has (where he's still in the bloodied RPD uniform) and the interrogation tape from the old DSC, it appears not longer after Claire left to go find Chris, Leon & Sherry got kidnapped by the government. Thus, I think its safe to assume Leon was already being trained when he got the email from Claire. We don't know if he had a laptop or if he like logged on to a library computer or what, but we do know he got Claire's email and then went and found Chris, passed that info along, and that is how Chris found out about Rockfort Island.
That's the current timeline of events, but its quite possible CVR may shake some of this up and provide more details into the specifics.