I figured what my mistake was and under which condition the panel's MeasureOverride is no longer called on certain changes for size-related properties.
My panel called Measure on children with the exact size the children should have, rather on the size of the panel.
A panel doesn't get it's MeasureOverride method called when children begin to desire more space than was told to them is available in the last Measure call - which makes sense.
Summary: The parameter for the Measure method you call on a child must denote the space the parent panel allots to all children, not just the one Measure is called on.