re: I am unable to update from 8.5.4 to 8.5.14. The wheel keeps turning and turning and never stops. Maybe I need an intermediate update in between?
No, you do not. You can upgrade 8.5.4 to 8.5.14. After you click upgrade, and the wheel spins for a while, what happens when you refresh the page? Is Connections updated or is WordPress reporting that it still needs updated?