Good list of potential catalysts. However for 2) I wouldn't say that Electrify America's investment is still several years off.
Cycle 1 goes from Q1 2017 through Q2 2019. Initial locations are already in development, and new charging stations will be operational starting Q4 2017, which is now. All 450+ new stations funded during $300M Cycle 1 investment will be operational by Q2 2019.
Given that Chicago was ranked 3rd in list of markets to prioritize, I would suspect that at least some funds would be dedicated to the Chicago market by now.