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We do something like this, but... from the "bottom up". i.e. when a Timesheet is approved, update Actual Start Date on WorkItem.ParentProject.
However, you can probably do what you're asking for by creating a new variable, update variable and run on Aggregated Timesheets, then when updating the variable do a compare of variable.ActualStartDate and TargetObject.ActualStartDate.
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