I was thinking of a list view but wanted to see if anyone knew how to do it with the setup we currently have.
If you want to customize the rows of a data grid extensively, then i'd advice to use a Listview instead. A List view allows you to setup the data of the row including images and buttons more easily.
Of course a boolean for visibility is an option. Based on the boolean of the rows' Entity containers can be shown/hidden. By placing the button inside those containers you've got full control.
The main question should be: What are you trying to achieve with this?