One of the key parts of my work every summer is the creation of yearly retrospective documents for each of our programs, so perhaps I can offer some advice. I've read your outlooks for a few years now and they tend to run into a few issues: verbosity and repetition.
You should start with an introduction, analyze last year's outlook, begin with a general outlook, break down the months, and end with a conclusion. The repetitive index explanations can fit into an appendix of sorts.
You have a great deal of analysis to share--it just needs some tweaks in presentation.