Nice thread you started.
As they say, teachers there are many, students there are few. Most everyone wants to be a teacher, and few want to struggle or accept the fact that they are students. Interestingly, usually the more capable a teacher becomes, the less he or she is inclined to teach. And of course, vice versa - the less the student knows, the more the student wishes to teach.The spiritual process is always paradoxical.
The very essence of an enlightened individual is that he or she will by virtue of that enlightenment, be radical, because the "rules" of "appropriate behavior" no longer make sense to him or her because these folks now live in a world which does not differentiate, but instead unifies. That said, however, they usually abide by the rules in order to escape the inevitable attention that radical behavior generates, unless they are "making a point", as Jesus did. This is logical, because such a person does not relish attention, but instead, prefers solitude and often anonymity -- why would a person who does not consider himself to be special or separate want attention directed to what he considers to be a non-existent entity?
To put a metaphysical spin on this subject: a teacher of any kind, but particularly a liberated one, is a reflective surface for the student, against which the student applies all his or her consciousness, conditioning, associations, and expectations. This is why often the most liberated teacher eventually "creates" antagonism in the student, because the heat of the student's preconceptions, many of which the student is unable or unwilling to acknowledge, become apparent, but only by the process of "projection" from the student to the teacher. (Of course, the teacher creates nothing of the kind - it is the student's own dance that is projected onto the face of the teacher. The miracle of all of this is that the teacher supports, and often encourages this dance, for the sake of the student.) This is of course a great sacrifice made by a teacher toward the student - he or she is willing to carry the burden of the student -- does this sound like the crucifixion of Jesus? Well, that is what it was, after all. The teacher literally "lays down his life" for the sake of the salvation of the student - or - from a less esoteric vocabulary, the teacher gives up his time and energy for the sake of the liberation of the student, and does not expect anything in return. Contrary to the student's beliefs, who because of his less liberated view, assumes that the teacher gets great "return" for this effort, in the form of all worldly expectations, egocentric satisfaction, aggrandizement of name, fame, and so forth, the teacher actually receives nothing like that for this effort, and instead frequently receives grief and trouble in exchange for his sacrifice. Instead, the student, by projection, of course, envies the teacher's position, and wants to "be there himself", not knowing until he knows that the position he seeks is not what he thinks it is, nor does he want that position when it is finally reached? Paradox, paradox!
In other words, the purer the teacher (the less he projects of himself outward), the greater the ability that teacher brings to a student for the student to see himself through the teacher. There of course is a meeting here of minds - as Gurdjieff constantly pointed out, a teacher, in the area of esoterica at least, can only teach a student who is just one step behind him, and is unable to therefore teach those who are further "behind". Likewise, each student therefore is, or becomes, a teacher to the next lower step student, and so forth. Does this sound like evolution - I think so!
That said, the genius of Jesus, as well as the Buddha (Siddartha), and the other great founders of religions, is that they managed to be understood by ALL levels of students, despite frequently and apparently conflicting interpretations of their words by those followers. Perhaps this says something about the level of purity of the teacher, or, perhaps instead, it says something about the power of organized groups with history and time on their side?