Summary of passage: The Lord has anointed me (Jesus speaking) with the Spirit of the Lord to preach the good news, bind up the brokenhearted, and bring freedom and light as Jesus proclaims the year of the Lord’s favor and the day of vengeance of our God. Jesus will comfort and provide for those who mourn. He will give them a crown of beauty, oil of gladness, and praise as they will be oaks of righteousness for the Lord’s splendor.
The people will rebuild the city as foreigners will shepherd their flocks and work the fields. The people will be the priests of the Lord and be fed by the wealth of other nations. They will receive a double portion and everlasting joy. God will reward them with an everlasting covenant for all to see the Lord has blessed them.
Isaiah now says he will rejoice and delight in the Lord as a bride and groom does on their wedding day since God has given him salvation and righteousness. The Lord will bring righteousness and praise for all the nations just as He does for the seeds that sprout and provide abundance.
3a) The anointed one is indisputably the Messiah, Jesus. Anoint means to choose as if by divine election. The Lord has chosen Jesus to preach good news (salvation) to the poor, bind up the brokenhearted, and bring freedom and release from darkness–save from sin.
b) Because “the day of vengeance of our God” refers to Jesus’s Second Coming, not to His first. It wasn’t the time to proclaim it; only time to proclaim the year of the Lord’s favor. Isaiah 34:8 “For the Lord has a day of vengeance, a year of retribution, to uphold Zion’s cause.”
4a) They will have a crown of beauty instead of ashes (of mourning 2 Samuel 13:19), oil of gladness instead of mourning, a garment of praise instead of a spirit of despair. They will be oaks of righteousness displaying His splendor.
b) Personal Question. My answer: Released from the weight of my sins daily, comforted by God’s faithfulness and goodness, seen beauty where otherwise I wouldn’t have, been grateful and glad instead of melancholy and down in the dumps.
5a) The people shall rebuild the ancient ruins and restore the places long devastated. Foreigners will shepherd your flocks and work your fields (perform menial labor) as you will be the priests of the Lord and live on the wealth of other nations. The people will inherit a double portion and have everlasting joy.
b) In God’s faithfulness He will make an ever-lasting covenant with them so all who see them will know they are blessed by the Lord. They will be God’s testament to His faithfulness and goodness.
c) Personal Question. My answer: A wedding is one of the happiest days of people’s lives. Isaiah is as happy as the bride and groom to receive God’s gifts of salvation and righteousness. As seeds start to grow and we see them sprout, we see God’s miracle of life. All nations will experience God’s miracles/gifts of righteousness and praise as surely as He makes the seeds sprout.
Conclusions: I see God’s overwhelming blessings for His people, which is a sign of His incredible love for them. We see God’s love in providing a Savior and providing for His people’s needs as they prosper as a nation. He does this partly for the people but also as a testament to who He is.
But God doesn’t stop there: Isaiah says God will bring His righteousness and praise to all the Nations (most of us today). Yeah! Praise God!
End Note: I spent a bit of time on Question 3b. I was hoping to find a better scripture that spoke specifically of why Jesus didn’t want to address His Second Coming at that time in his ministry. I’d appreciate any additional verses or ideas. The following is the best explanation I found (scroll down to the commentary section):