RadPropertyGrid automatically generates RadComboBox as an editor for PropertyDefinition bound to Enum property. When you have FlagEnums, RadPropertyGrid generates FlagEnumEditor, not a ComboBox. When RadPropertyGrid is filled with a collection it generates CollectionEditor. You can find more information about it in this help article.
I would advise you to use a DataTemplateSelector to achieve this. Please refer to this help article. In this way you will be free to load different DataTemplates according to your custom conditions. Please, let us know in case you need any additional help on this.
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