Dates are not highlighted in Calendar when clicking on Show In Calendar button on Job definition. Also, the jobs are not simulating properly.
In this particular scenario, there were too many Special Days and/or Holidays that had already passed.
Issue was related to calendars. There were several Special Days and Holidays that had passed that I believe to be the root cause of the issue. Once the expired dates were removed from the calendars, the dates in the calendar would now show when forecasted and jobs simulated properly.