Jesus acted within a culture and a time.  I do not believe He would have any problem with women in leadership in today's world - because women are accepted in leadership today in ways they absolutely were not in those centuries ago.  There is nothing sacred about the roles - that was all human.  

Truth is God.  We are not God and we cannot possible know Him.  We can listen to the Spirit and try to understand what God is trying to say.  But everything we hear and see and sense is filtered through our own humanness - at every point in time we are limited in knowledge and influenced by human created culture.  It is foolish to think we have ever gotten it perfectly right.  We have always only done the best we could based on the limits we had when decisions needed to be made.

And it is the worst hubris to think we have ever gotten any understanding perfect for all times. 

I have faith.  You want certainty.  The two are not the same.