I was worried people would run into this quirk in the demo. We have several 'advanced' question generation strategies. You correctly guessed the one we're using in the demo; forming complex questions by finding another page in the same category as Ripken and pulling more facts.
Normally we pull a ton of related topic and try to pick the best, but to keep the generation fast and cost effective in the demo I limited the number of related pages we pull. So sometimes (like this case) you get something barely related and end up with odd disjointed questions.