Training his hearing begins by studying basic acoustics concepts and the way to modifiy them in our room...
Listening 100 different speakers and 100 different dac and 100 different amp and pre-amp has nothing to do with training his hearings..
This is what sellers and reviewers do to sell you a new necessary "upgrade",...
Half the time useless...
Training his hearing has nothing to do with the gear price, branded name etc
I would hope that even those who talk about "training" the ears would agree that an objective foundation is needed for such training. Otherwise, the whole situation becomes quite murky, as one can be "trained" to prefer highly colored sound. In a sense, we all get trained to prefer our current systems, as has been pointed out many times.