I really enjoy the stylistic touch of writing from the perspective of a future history book.
I've recently been toying with the idea of doing a timeline but from having it open from the vantage point of just average people discussing politics fifty years or so in the future. I could very well see a generation or so in the future this current era being looked back on as the "failed outsider age" in the same way we look back on the early twentieth century as the progressive era and comparisons between Obama, Trump and they're respective movements being made and seen as similar since oftentimes the further away you get from an era the more the nuances of that era are missed. Like how people now would see TR and Wilson as both emblematic of the progressive era despite significant differences in there worldviews. But yeah, keep up the good work!
Exactly. Woodrow Wilson and Teddy Roosevelt were similar people in terms of the ideology (although with important differences). As it would turn out the Populist era presaged the New Deal two decades later.
You should absolutely give your timeline a shot. I have a couple of notebooks here filled with notes, sketches of stories, ideas, and plain out writing my thoughts.
The timeline helps me articulate where we're going as a society and what that means for our future. For me I feel the next decade is going to be extremely consequential and will be a turning point. So I write and as you can tell I try to follow the trends of history.
I try to write in three voices. 1) Newspapers 2) History 3) TIME Magazine pieces. And occasionally I do meta to guide the reader.
Anyway, just some thoughts. I look forward to your timeline. 
Excellent thoughts, thank you!
