Revelation 14:1  “…with Him one hundred and forty-four thousand, having His Father’s name written on their foreheads”
Probably the same group mentioned in chapter 7 revisited.

3  “…no one could learn that song except the hundred and forty-four thousand who were redeemed…”
Only they could understand the song as they were the ones who experienced it.  As the Bible says the angels wonder about us, the redeemed of Christ.  They have always been perfect, we have been redeemed.

1-5  Seems to be a conclusion of what is mentioned in chapter 7.  This is what happens to the ones sealed there.  The fact that John sees them on Mount Zion with Christ may refer to them returning with Him to be part of the millennial kingdom.  Not sure if they were martyred by the beast or if they were sealed from harm and entered the millennial reign without dying.  If the latter, would have to die at some point I would think.  Not given enough information on that aspect to even speculate.

6  “…having the everlasting gospel to preach to those who dwell on the earth…”
All have a chance to hear, but not all choose to do so.

9-11  “…He shall be tormented with fire and brimstone in the presence of the holy angels and in the presence of the Lamb…”
Those who worship the beast, who choose to follow satan rather than Christ, will eventually be thrown into the lake of fire with satan, his angels, the beast, and the false prophet, the second beast.  Not something to look forward to.

12  “…the patience of the saints…”
The saints are avenged for what happened to them.  God is making all right.

13  “…Blessed are the dead who die in the Lord from now on”
Not sure, but if this is pointing to a point just after Christ’s return when all accounts are settled, he may be referring to those who knew Christ who entered the millennium without dying.  They will eventually die to end the sin nature with which all are born, but no pain in that death as Christ will be reigning on the earth.

14-16  “…on the cloud sat One like the Son of Man…and the earth was reaped”
Obviously Christ, the Son of Man.  Assuming the reaping is of those who belong to Him.

17-20  “…the angel thrust his sickle into the earth and gathered the vine of the earth, and threw it into the great winepress of the wrath of God…winepress was trampled outside the city, and blood came out of the winepress, up to the horses’ bridles…”
Reaping of the enemies of Christ.  Results of a battle, perhaps one of the ones referred to as a Battle of Armageddon.  Says it was trampled outside the city.  May refer to Jerusalem which might make it the battle of Ezekiel 38-39.

Note:  By this point it is obvious that some of what John is seeing and its corresponding events on earth are overlapping.  Obvious why Revelation is difficult to fully interpret with total confidence.  Not the content, but the complete timeline between heaven and earth.  Makes sense as heaven is outside of time while earth is not.

I hope you enjoy reading and studying His word.  May it accomplish what He desires.  Please feel free to comment or post questions.  Thanks for reading!

Scripture taken from the New King James Version®. Copyright © 1982 by Thomas Nelson. Used by permission. All rights reserved.