I did find some of the questions seemed to be repeated, not sure if this was ignorance on my part, or encouraging us to think about things from several different angles.

I'd suggest that situation perhaps refers specifically to where they are, if you like the environment that they are in, including the problems and opportunities that offers them. Condition then might be considered their 'inner' world,. You can consider this intellectually, e.g. what is on their minds right now, and/or emotionally, how do they feel, are they happy, apprehensive etc.