Re: retrograde Mercury and progressions, to elumen
His mercury is only has very wide orb sext to moon, but quincunx to Jupiter and Asc which will make communications more difficult. It helps being angular cos 7th 'other people' is where he wants to communicate, espec about emotions (cancer) and sext to moon (women) Merc Trine to N Node (pisces) suggests that his Lessons and about communications will be connected to emotions and the right people will cross his path in neighbourhood to help and assist him on his journey.
Also merc is conj 8th house and is said to have more effect there, again scorpio's house, does not want to communicate on anything trivial, but deep and meaningful and wants these communications to be transformative. Again it's all water and emotions. His chart lacks the element of air and only 2planets in air house ie:7th which is naturally libran ruled, but Gemini/Merc in his case. Trouble with these two are they are restless, procrastinating and indecisive. Does he show these traits?
At what age will mercury go direct? Spiritually I believe we are all here to learn certain Lessons with certain people at certain times, doesn't matter whether we are in primary school, secondary, college or university. We are all on this upward learning spiral.