I'm not so sure I would be agreeing with the initial premise, actually - surely it's more a question of different teachers being better for different pupil temperaments - and some being more flexible and adaptable to a wider range of outlooks than others?
I know for instance that it was a female teacher who was able to click well with my son, rather than the male one he also had - the switch was made part-way into the journey into puberty, but turned out not to have been a good one for him.
Equally, in my own experience of male and female teachers, I'd say that their sex, and mine, has made absolutely no difference at all to how well the teacher-pupil relationship has functioned, at any level and any stage in life I happen to have gone through - I cannot think that it would be likely to, either, nor can I see that adolescent boys present any particular challenges which would be different from adolescence in girls. The one single exception in music teaching might be singing for the changing male voice, but it doesn't sound as if this is what you're meaning in this case...
When it comes to dealing with teaching boys with changing voices, as I've mentioned on TOP several times the jury is out, but currently collective wisdom is to teach through the change and be sensitive to the known five stages of vocal development.
What is needed is a teacher who understands these and makes sure that he or she does not force lessons into falsetto all the time. Even counter-tenors need to know how to blend with their natural voice, and those who spent too long in falsetto too early can find this a real problem.
As long as the boy cum man realises you will bung things up the octave so you can sing them, there isn't a problem.
The only voice I feel uncomfortable teaching is the counter-tenor voice, but as a coloratura soprano my flautino register is the female equivalent to falsetto, so unlike many female singers I do have some understanding of the techniques involved, but to demonstrate them means working above top C!