How far is too far?

In pushing the theological boundaries how far is too far? I have been thinking a lot about TSK post here

on Acts 15 and recognise that as missionaries come back and tell the stories of how they contexualised the gospel, that the teachers did indeed make some sense these stories and grounded them in the biblical narrative. A couple of thousand years on are todays teachers willing to do the same leg work? As I try to make sense of where God leads through mission contexts I am not sure if the teachers will catch up. As the missionaries move on and culture shifts if they do not keep up it takes a Luther or Calvin to fill the vacuum (My fear is they would never be heard in the myriad of voices of postmodernity). If Dave comes back with a reinterpretation of Blessed are the mourners through his experience with the young people here that does not fit into the traditional narrative who is to say they are right and he wrong. Where should the weight be, with missionary or the teacher?