Jesus didnt hold back...that's for certain.
He wasnt trying to curry favor - which is why the Pharisees really dispised Him.
His comment about the dead burying the dead goes way beyond that. It was not directed to someone who was trying to kill him, but too a friend, a disciple even, someone that he loves and who loved him.
Just think for a moment of how monumentally cold that must have seemed.
What a thing to say to someone whose father had just passed on!
Just to contextualize, to compare to current threads, if I would have responded to people leaving here and others lamenting their passing with a 'good riddance', or worse, 'let the dead bury the dead', I think that most normal people would consider me to be mean and ill-mannered, to say the least. (not that I would ever do such a thing

)
But go one further, you have a thread about your cousin here, that I avoided because I am not the best at offering comfort.
But if I would have responded the same way that Jesus did to you in that thread, or worse, if I would have responded in a similar thread about your mother, this would be monumentally, monstrously shocking. How could it not have hurt you to the very core of your being?
Even with hindsight, knowing that Jesus was embarking on the singularly most important even in history, and that all disciples really ought to be there, I daresay that the shock of these words to most Christians is hard to grasp. The sarcasm in the words, being said by the God of Love, has the power to rock our world and swallow up all our preconceived notions of what love is.
We can explain of course, but sometimes explanations just get in the way.
The truth is, life in the Spirit has its terrifyingly awesome, even awful aspects to it.