I have this case
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Longe
I originally looked at this using IsSharedSizeGroup but hit a roadblock with making it dynamically apply to things instead of explicitly wrapping items. In this case, creating an AttachedProperty in code or another code based solution may in the long run be better then a XAML only approach. However, to create a purely XAML solution we can make use of the SharedSizeGroup property on a ColumnDefinition to share the sizes of each element and then use set the IsSharedSizeScope property on the WrapPanel. Doing so will make all of the contents in the WrapPanel with the same SharedSizeGroup share their width for columns and height for rows. To wrap the ComboBoxes and possibly ComboBoxes that are not currently in the XAML but will be added to the WrapPanel, we can create a Style and re-template the ComboBox to bassicly wrap it with a Grid.
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Foo
Here we are re-templating all CheckBoxes without a style inside the WrapPannel to instead be CheckBoxes surrounded by a Grid. However, because of this we need to re-bind all of the CheckBoxes properties that we want to maintain. While that could become burdensome, it also allows for a pure XAML approach.