I don't think that the checkbox ever worked correctly. It was more of a visual indication. Context menu is to be used to change the display. In v0.9.25F, I've disabled the checkbox (for now anyway) until it can reliably work
Since there isn't any indication for the user that some options are to be found via a context menu, I wonder if those (context menus, where ever they are in the properties pane) could be replaced by a Drop Down menu maybe accessible through a button called "options" (o, even better some "Option" icon...).
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