We would need to better understand the use case in order to provide feedback. Creating dependencies between parent and children is not recommended, one of the reasons being the dependency loop you ran into. There are ways to force the duration of a sub item to match the project, but it would require configurations and would go against the way the system is designed to work (milestones drive the project duration, not the other way around). I would take a step back and see if the project structure makes sense for the type of projects you are running.
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