Okay, I played with the Sermon Assistant, both Illustrations and Questions, and couldn't force it into any silly responses but only into vapid responses. The responses always reflected the options selected to a reasonable extent. My only problem was I couldn't come up with any reason I would ever use the tool - the results were never better than I would have created myself nor taking things in a direction I hadn't thought of.
But I did come up with a related tool that would be useful - an assistant that would look for the connections between the homily and the liturgical year and the liturgical texts of the day to which the sermon is assigned. Unfortunately, that is not a tool we are offered.
I would like to hear from some beta testers who are more enthusiastic about the tool.