That white car with the blue and red light bar on top in the middle of photo #3 is probably a cop car or security car. I wonder if its occupant was waiting for Jim to come down from his perch.
Jim's perch seems to be higher than the street lights, so I went to Google Maps to see where it might be. The neighborhood seems to have changed. I couldn't find a spot that fit. But, if you scroll up along Union or Poplar, you'll be rewarded by seeing the Key System curves at 12th St and West Grand Ave.
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maps.google.com]