Don’t use the data view inside the custom content column. Instead of the data view use the list view and then try it.
You are stretching this new widget to and over its limits. Lovely. Pitty that it does not hold up and very unlikely that this gets resolved anytime soon. I kind of expect this behavior to be normal again if you do not use visibility in the Datagrids. So just remove the visibility-settings and try again. Yes, you will see multiple buttons and that is not what you want, but just as experimental test. Does it indeed show the buttons?
Another test: what happens if in you second image ‘with filter’, you chang the sort-order of Status. Is still line 1 correctly showing the buttons and line 2 still empty, or did that change too?
Can you perhaps add a widget and use the dynamic class to add a different class based on the status-value. And style the button based on that?