Hello Josh. I’m guessing by the circle and dot and yellow ring you mean the tool itself? I’m not sure but the tool visualization goes away for the moment the tool is in action, as soon as the action is confirmed, the tool visualizer comes back.
When it comes to pressing B, where your muse pointer is matters. Perhaps you have it too close to the face. Try getting your mouse pointer a bit farther away. And remember, when you use a tool and then you want to use another, for example you use E to Extrude and then I for inset, you have to commit and accept the use of the extrusion first. So you extrude and click or enter so the extrusion takes effect, then you use I for inseting.