(J) needs your help as he is blocking himself by his questions about the Journey he has taken thus far. His aims are far reaching and he must learn to take small steps instead of trying to go too fast – as is his wont to do.
Try telling him that he should just do breathing and Mantra Meditation for a week or so in order that he isn’t looking for something each time he sits down, as the expectation is getting him nowhere.
You have gathered that his Path, like (N)’s, is unconventional and this will continue. This is no bad thing as you are well equipped to deal with that.
With regard to how far he has come. If you are going on a Journey the Landmarks are important, you need to see the major ones at least, even in the wrong order.
With him doing the techniques before his Initiation this has certainly been detrimental to his Meditation, but all is not lost. As you know, it is possible to have previews of the Landmarks and this is what has happened to (J).
(G) has been sent to show him the Way, literally. Get them to Meditate together and compare notes, (J) needs a mate who is at the same stage as him.