I've come to believe two simultaneous understandings for this scripture. They can be accepted at the same time because one nests inside the other.
The first understanding is found within the cultural context of ancient Israel for burial customs. (I'm only familiar with these customs from what I've read.)
Apparently many ancient mid-east cultures buried their dead twice. The first burial was in a family tomb or cist. After decomposition, sometimes years later, there was a second burial ritual in which the skeletal remains were placed in a box sometimes referred to as an Ossuary. (Presumably this was done to make more room in the family grave.) In a culture that took seriously the command, "Honor thy father and mother", it is easy to imagine that these two burial rituals, sometimes years apart, were taken very seriously as duties before God. Obviously, such a sense of duty to a young devout man, waiting for the second burial of his father, would create a conflict in his conscience about picking up and traveling with Jesus.
I believe the second, and deeper understanding of this passage is that Jesus is asking for our willingness to seperate from the very cultural and religous customs that once defined us, so that we may follow him and find a new identity in him.
Interestingly enough, today's entry for Oswald Chambers, captures this very point, especially in regards to family connections.
"In the Old Testament, a person’s relationship with God was seen by the degree of separation in that person’s life. This separation is exhibited in the life of Abraham by his separation from his country and his family. When we think of separation today, we do not mean to be literally separated from those family members who do not have a personal relationship with God, but to be separated mentally and morally from their viewpoints. This is what Jesus Christ was referring to in Luke 14:26."
"If anyone comes to Me and does not hate his father and mother, wife and children, brothers and sisters, yes, and his own life also, he cannot be My disciple."
(The Message paraphrase has a 'gentler' rendering...)
"Anyone who comes to me but refuses to let go of father, mother, spouse, children, brothers, sisters—yes, even one's own self!—can't be my disciple."
So, with these two perspectives working together, I believe Jesus was asking the man to cut some profoundly defining cultural and religous ties in order to become a disciple. These are just my own beliefs on the topic. I'm interested in seeing what inisghts others might have on this passage. (And other passages like it!)
MC.