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We have added a bunch of Initiative issues in a Jira Cloud project and are using those to break our work out into Epics. The Initiative issues have the "Start Date" filled in, and I thought that would be used to fill in the Target Start Date in the Portfolio plan, but they remain blank. We do have Target Due Date syncing correctly - what needs to be done to get the Target Start Date also syncing?
The target Start and end dates are a method to set a projected possible time frame that is used as a place holder to try and align the actual estimates and requirements during the calculations with what you want to have as the outcome. They are intended to be entered manually and not sync with the calculation to give you a what should be done view to contrast what can be done based on the calculated schedule.
This is covered in more detail in the "Add target start and target due dates", but specifically noting the comment:
Adding target dates is helpful when planning work for your team. When you're at the start of planning work, you may have an idea of the tasks that must be completed, and when these tasks should be completed. Most of the time, you won't have more information beyond that. In such cases, using target dates — specifically target start dates and target due dates — helps you set high-level targets for the work you're planning.
The start date of the initiative is going to be calculated based on the initial start date of the earliest issues start date in the lower hierarchy levels. i.e. if a story is nested in an epic that is a child of that initiative, then when the first story starts, that date is cascaded up the hierarchy to the top level start date because the initiative starts when the work on the child issues does.