Re: Chapter 8: The Five Year Plan
It will be helpful if players work out some back story that would connect to Fort Griffin. It doesn't have to be immediate or continuous over the timeline. So, for example, it's viable for characters to go to Deadwood in 1875 before making their way to The Flat in 1877.
The idea of picking a couple of key events, including any on Travis' list, is fine. But as Randy points out, keeping an eye on connections to Shackleford County, Texas will make the transition easier. For example, Randy's idea to take up a career in prizefighting would provide an easy connection (Shannsey's saloon, owned by an ex-prizefighter).
Events that are in or near Texas (e.g. the Second Battle of Adobe Walls, Buffalo Hunting) could make connections more viable. Also, a number of famous personages ended up in Fort Griffin in the mid-1870s. Finding connections to them in previous years (Forest Gumping it, if Travis pleases) whether in Texas or somewhere else will help.
A few examples: Ben and Billy Thompson, Doc Holliday, Big Nose Kate, John Selman, Sheriff John Larn, Sheriff William Cruger, Lottie "The Poker Queen" Deno, Frank Thurmond, Wyatt Earp, and John Wesley Hardin.