As I mentioned, focus a bit less on chronology and more on the themes and overall arcs of each moment in Chris' life. Don't be afraid to foreshadow, recall, etc.
I think the early episodes are great at that. They have an overall feeling of Chris" early years and childhood that are not strictly chronological. You learn a lot about him before being discovered by the internet.
As I mentioned, I haven't watched the latest episodes because I'm just a faggot that will seethe whenever Chris is referred to as a true and honest woman, but I also dread that those long periods of time when Chris just tweeted or didn't do much boil down to the date of his posts and online presence.