Thank you for your question regarding I Thessalonians. chapters 4&5.  You are right; it is hard to find help on this subject.  We can all appreciate Peter telling his readers that concerning these things Paul had written some things hard to understand. (II Peter 3:15-16) 
 
Concerning the passage:
Then we who are alive and remain shall be caught up together with them in the clouds to meet the Lord in the air. And thus we shall always be with the Lord. (NKJV)
I believed for a long time that there were two comings mentioned here.  I finally gave that up, not finding anything to support that view except my preconceived ideas about what "caught up together with them in the clouds to meet the Lord in the air" meant.  It took a long time to shake the view that Jesus was going to come, and, if I was alive, I would see Him and be transported to Him as He appeared in the clouds with the faithful who had already died.
 
That was the difficulty, shaking the old thoughts.  I now believe that Jesus did come in the clouds just as He promised He would do in Matthew 24:30 and 26:64.  This was to be in that generation.  It is recorded in Acts 1 that angels (men in white apparel) told the apostles that they would see Jesus come in like manner as they saw Him leave.  They saw a cloud receive Him out of their sight.  The prophecy of Daniel is fulfilled by Jesus coming in the clouds, Daniel 7:13.  And one last note is that John in Revelation, writing about things which must shortly come to pass, says in verse 7:
Behold, He is coming with clouds, and every eye will see Him, even they who pierced Him. . . .
We have no record of the moment when Jesus came in the clouds, but we have His promise and the promise of the apostles and prophets.  I choose to believe Jesus and the prophets rather than what has become the standardized teaching that this event has not yet happened.  Why do most teach that the event is still to take place?  I believe it is because they have understood the language of the scriptures in human concepts.  Clouds are often spoken of in passages about judgment.
 
Jeremiah 4:12-14
A wind too strong for these will come for Me;  Now I will also speak judgment against them.  Behold, he shall come up like clouds,  And his chariots like a whirlwind.  His horses are swifter than eagles.  Woe to us, for we are plundered!  O Jerusalem, wash your heart from wickedness,  That you may be saved.
Ezekiel 30:3
  For the day is near,  Even the day of the Lord is near;  It will be a day of clouds, the time of the Gentiles.
Joel 2:1-2
Blow the trumpet in Zion,  And sound an alarm in My holy mountain!  Let all the inhabitants of the land tremble;  For the day of the Lord is coming,  For it is at hand:  A day of darkness and gloominess,  A day of clouds and thick darkness,  Like the morning [clouds] spread over the mountains.  A people come, great and strong,  The like of whom has never been;  Nor will there ever be any such after them,  Even for many successive generations.
Nahum 1:3
The Lord is slow to anger and great in power,  And will not at all acquit the wicked.  The Lord has His way  In the whirlwind and in the storm,  And the clouds are the dust of His feet.
Zephaniah 1:15
  That day is a day of wrath,  A day of trouble and distress,  A day of devastation and desolation,  A day of darkness and gloominess,  A day of clouds and thick darkness.
At least two things happened as a result of the destruction of Jerusalem.  By definition, it was a judgment but it was also the time that the kingdom of righteousness was received as an inheritance to the faithful.  Hence John saw:
the holy city, New Jerusalem, coming down out of heaven from God, prepared as a bride adorned for her husband.  And I heard a loud voice from heaven saying, "Behold, the tabernacle of God is with men, and He will dwell with them, and they shall be His people. God Himself will be with them and be their God.
Paul said, "We shall always be with the Lord."   Are we not now with the Lord?  I believe that we are.  I also believe that those who lived when the apostles were writing had not as yet received this blessing.  They were awaiting the return of Jesus that they might be presented to Him, holy and without blemish, Ephesians 5:27.  In those times they were receiving (present tense in Hebrews 12:28) a kingdom which would not be shaken.  We have now received that kingdom.  Hebrews 12:26 refers to God's promise to shake the earth and heaven.  The kingdom of Israel as God's people was removed, verse 27 and Christ's kingdom remained.  I believe that I Corinthians 15:24 was fulfilled when Christ's kingdom was presented to God as the one which remained.
 
I will close for now hoping I have cleared up some things for you.  I may have stimulated more questions.  If you do have more questions, I will be glad to offer my thoughts for you to consider from the scriptures.