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It's my understanding that Rollup Analyses are only capable of rolling up attributes from elements directly beneath themselves. You can read more about this in our documentation. If you want to roll up an attribute from grandchild elements you would need to do as you suggested; rollup Grandchild Element's attributes to Child Elements, then roll those up one more level.
Thanks for confirming this. I looked at the documentation that you provided but it does not state that rollups only apply to the immediate children.
It would make things clearer if the documentation explicitly stated this.