Ryan,
I think that the statement about things generally being confusing for people is a great one.
I already use the "does anyone have any questions, is this making any sense" type of questions. I can see, however, that using something like your example is an easier way for someone to admit their confusion, without feeling like they are stupid for being confused. It's a softer way to offer them more clarification or information without expecting them to just throw themselves out there with "I don't understand".
Thank you so much for the suggestion, and I look forward to trying to implement it. It is often hard to get the students comfortable asking questions in my live chat class sessions and I think this could be a great idea.
Best wishes,
April