The strangeness of Jesus’ stories is always part of the confrontation. There is this man who plants a vineyard and then goes away. Are we supposed to think this is God? Does God plant Israel and then go away to another land for a long time?
Also, this man doesn’t do things the right way. We all know how to do things. If we send a servant to collect the money and they abuse him, and — for whatever reason — we decide to be patient and send a second servant along and they abuse that one too…well, at that point, we’ve learned our lesson. We don’t send a third. When they abuse the third, how does this man (God?) send his son “that he loves” expecting a different result.
There is the secondary problem of the tenants. Under no system that I know of, when you have a man who is powerful enough to kill you, is there a rule that says, “If you kill a powerful man’s son, you get the rental property where you’re staying.” That’s just weird. It makes their actions especially cruel and seemingly designed to strike despair into the heart of the land owner.
There is always the overwhelming urge to historicize it. He was talking to 1st century Pharisees etc. You can actually read the thing and think of how it affects others without really doing the work that Jesus is asking you to do.
Where is the vineyard that I am protecting for myself?
What crops from my vineyard am I holding back as my own?
Where is the place where I have been patiently asked, too patiently asked — to the point where it doesn’t make sense that so many messengers keep coming — to turn over some of the fruits of my labors?
Where do I actively work to keep Jesus and his messengers away from my work?