Verses 1-12
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In this parable, we're reading about the story of the Hebrew people.
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God sent the prophets to Israel, and lastly, He sent Jesus to them, to encourage the Jews to repent; but they did not. They rejected Jesus, and yet, He became the “chief cornerstone”
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God—the vineyard owner—takes it personally when we reject the messengers He sends to us.
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Unlike the Jews, don't reject any of the words of Bible. If we reject the Word, we are rejecting God. Heed all of the Word!
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Verses 13-17
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The Pharisees' test was this: “If Jesus doesn't respect human institutions, then wouldn't He say we shouldn't have to pay taxes to Caesar?”
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If this was the case, Jesus would not be submitting to Rome, and that would make Him a threat to Rome (this could have created a way for them to turn Rome against Jesus, to kill Him).
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But if Jesus said that they should all pay taxes to Rome, that would make Him less popular to the public, because the Jews hated that they had to pay Rome.
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Jesus' answer was genius. It was Rome's currency, so it belonged to Rome. This world's money has this world's image, so we shouldn't worry about having to pay it back to the world.
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And since we receive the benefits of having a ruling government, we owe taxes to it(Romans 13:6-7). So, pay your taxes, and don't worry about the money the government asks from you.
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Conversely, God's image is stamped on us. So give your life to God in obedience to Him! You owe your life to God!
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God isn't concerned about the money going to Caesar. He's concerned about our lives not being given to Him.
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Verses 18-27
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See teaching on Matthew 22 for more details.
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Marriage between man and woman is an experience for here on earth. It will not exist after Christ returns.
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So, don't be too attached to marriage, nor let your spouse become something that distracts you from your relationship with God (1 Corinthians 7:29-31,35).
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Verses 28-34
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See teaching on Matthew 22 for more details.
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Make loving God and loving others your focus, and do these things to your fullest ability.
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Jesus said that loving Him is about obedience to His commandments (John 14:23). So...
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Your body, your abilities, your personality, your emotions, your logic, your thinking-power, your pursuit of understanding and knowledge...use all these things to grow in obedience to the Word! Doing this is loving God and doing no harm to Him.
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In obedience to the Word, you will also know what it means to love and do no harm to either yourself or others.
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Remember that love is the focus! Do everything in the Word because you want to love God and love others!
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Verses 35-37
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Jesus, although He falls in the lineage of David, is not really a son of David (not biologically).
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Because David calls Him his Lord, Jesus is really the Son of God!
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This was meant to prove that Jesus is more than human.
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Verse 37. It is often that the common people hear the Word gladly, while the rulers and teachers do not. Remember this, and be thankful for the humble people that listen when you share the Word!
Verses 38-40
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See teaching on Matthew 23 for details.
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Don't be a religious hypocrite, and avoid leaders who are. Remember that religious hypocrites will experience a harsher punishment from God.
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You can spot someone like this because they seem to invite praise from people and they are very public in their displays of piety.
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They also extract finances and favors from people, exploiting the gullible.
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Verses 41-44
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Understand that generosity is measured by the percentage of what you have that you give, not the dollar amount that you give (2 Corinthians 8:12).
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Whatever generosity is to you, give; and give cheerfully. Know that God loves it when you give well from what you have!
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Also notice the pride of the rich, doing charitable deeds likely for self-congratulation and seeking reward—something Jesus denounced in Matthew 6:1-4. If we are like this poor widow, and will not "let our left hand know what our right hand is doing", we will do good at personal cost and sacrifice. Thus, giving sacrificially (and being content with personal loss for the kingdom) will teach us to do good without seeking gain or reward.