Comments:

As usual, my improvised color-coding scheme is employed on my translation.

11:14a

     This time context here, I believe, is 937 days into the period of great tribulation, the time when the trumpet judgements of Revelation are manifested.  The evil beast King of the South will be embroiled in a conflict with the Muslim nations that surround present day Israel (14b).  The evil beast King of the North will join forces with the armies of the King of the South to attempt to confront the returning Lion of Judah.

11:14b

     The “sons of the robbers of thy people” are those who adhere to the false religion of Islam.  Muslims believe that the Mahdi is the restorer who will come at the end of time to establish the reign of justice and righteousness.  This is “the vision” referred to by Daniel.

11:14c

     The efforts to “establish the vision” are not detailed here.  We can know, whatever those efforts may be, will be against the True Savior of the World, Judah’s Messiah.

11:15a

     Time-wise, 15a moves us to the time before Armageddon, to a time prior to the commencement of the thousand-year reign of Messiah, when the King of the North will come into “the city of fortresses” (Jerusalem) and seize it.

11:15b

     The followers of Messiah will not be able to defend themselves against the might of the King of the North and his genetically altered mutant army.

     Thus, 11:14-15 as a literary unit is reporting the idea that the evil beast kings will be involved in conflict.  Verse 14 speaks about the conflict between apostate Israel, ruled at that time by the evil King of the South, and her Islamic nations that surround her (essentially, the Edomites, Ammonites, and Moabites).  These people will attempt to install the Mahdi.  The Mahdi is a figure in Islamic eschatology who is believed to appear at the End of Times to rid the world of evil and injustice.  Of course, this is a false savior.  Verse 15 then reports that the evil beast King of the North will join in the fight, allied with the King of the South, at least in relation to defeating the True Messiah, who “shall come against him” (v16).  It is probably true that the King of the North joins in the fight primarily for the reason of mustering enough might to defeat the common foe of both the south and north, the Lion of Judah.

11:16a

     This verse shifts the attention back to the Lion of Judah, who shall thereafter “come against him,” the evil King of the North.  If we remove the verb clause “who shall come against him,” what remains is “But he shall do according to his will…”  As my color-coding indicates, this can be read explicitly as, “But the Son of Man shall do according to the Father’s will…”  This of course we expect from the Father’s Son, the Lion of Judah.  The remainder of 16a logically follows.

11:16b

     The “land of stateliness” is the ancient land of Judah and by implication, the land surrounding Judah, that land promised to Abraham.  This land shall be finished by Messiah’s hand, a figure of speech indicating that the state of affairs brought about by Israel’s rejection of the Father’s ways and then of their Messiah, whom the Father sent, leading ultimately to the corruption of the two beasts and the Mark of the Beast, will be set right again in the end.  Verse 16 is a powerful summary of the plight and eventual resurrection of Israel.

11:17a

     Verse 17 is speaking in more detail now about how the Lion of Judah will return with His followers (“faces of him”) in tow.  The Two Witnesses (“upright ones”) will also be part of the entourage.  17a is speaking about the literal processional-like, physical movement of Messiah and the entourage that will accompany Him back into “his own land,” Judah.

11:17b

     Verse 17b emphatically declares the veracity of 17a!

11:17c

     The Lion of Judah will surrender Jerusalem over to the evil King of the North.  We can be assured that this is the Father’s will, though it may not seem consistent.  The “daughter of women” is a figure of speech meaning the city of Jerusalem.  The King of the North will corrupt “her.”  Although the exact details of this are not stated, we can safety surmise that the Mark of the Beast and other evil practices will take their toll on those living in this beleaguered city.  Those who are destined for damnation may regret this station but nevertheless live without remorse.  Still many others will probably exist without succumbing.  

11:18a

     Here we see a tactical maneuver executed by the Lion of Judah, where, after the encounter at Jerusalem, He “turns back” to the “coastlands,” with a deployment of His followers, who He stations along the coast.  This is fascinating because of its detail and because it reveals that a real battle is taking place between Messiah and His enemies.  Messiah is posting guards, so it appears, along the coast, just as a military commander would do for the purposes of observation/reconnoiter and perhaps kinetic engagement of the enemy.  It is hard to envision any other purposes for this tactical move on the Lion of Judah’s part.

11:18b

     This verse snippet is again fascinating because it reports that the Lion of Judah will put an end to the “mouth” of the evil, King of the South.  Yes, the evil imposter King of the South is in view here because his demise is at the hands of the Lion of Judah is this of course is contemporary with the return of the Lion of Judah.  Very simple.  The Lion of Judah comes into the land of Judah, where he deposes the evil, imposter King of the South.

     Like a roach infestation, Messiah “eradicates” the “captain of reproach,” who is the evil, King of the South.

From that point forward in time, Messiah is the (true, legitimate) “King of the South.”

11:18c

     18c states that the slanderous reproach spewed by the evil one ruling over the land of Judah will be used to judge the true state of affairs regarding the imposter beast.  The deposed beast will be seen in all his depravity and lies and conversely the truth of beauty of the Son of Man will shine.  This “revealing” of this evil beast ruler may not occur at the time he is deposed because this evil beast will again face the Lion of Judah for judgement.  So the lies he shall speak may by replayed at his judgement … and that event does not happen at his dethronement.

11:19a

     Verse 19a reports that after the imposter beast ruling over the south is deposed, the Lion of Judah will then “turn His face” towards “his own land,” a reference to Judah.  Messiah will move inward from the coastline, along with His entourage, and come against the evil, imposter beast King of the South.

11:19b

     Here, in fact, we read that very thing: Messiah defeats the evil King of the South, who “stumbles and falls” and is thereafter “not found.”  19b is a sub-nesting within the overall group, but the differentiation suggesting this sub-nesting is not sharp since 19b is really the result of v16-18 beforehand.

11:23a

     This is the companion verse to 11:19b.  It adds the additional detail that “the league,” a reference to those bearing the Mark of the Beast who survive Armageddon, will continue to practice dark arts (sorcery and witchcraft, for example), and be a resource used by the evil beast King of the North, who retreats back to the north following the defeat at the battle.  So the ramifications of removing the evil King of the South is that the evil propagates onward with “the league” of those who followed him.  19b // 23a is a succinct disposition of the evil King of the South, which is that of death in this physical realm. 

11:23b

     This verse portion begins the complementary half of 11:14-19a.  The Lion of Judah will return to “his land,” the ancient land promised to Abraham … well, initially a small portion of this land.  The same land where the Lion of Judah was born and where He was crucified.  He and His followers will be the “small people” (relatively few in number).  Over time, the nation will grow numerically through births and probably emigrations.

11:24a

     “stout ones” has a meaning that would be better understood as “mighty ones” or “ones with a heavy build,” not to be confused with short or overweight.  The nuance of the meaning of “stout” has changed over time.  These are those who will have received the Mark of the Beast, which will have genetically alter them, causing large musculature and other mutations.  The army of the King of the North will be physically powerful and resilient — truly formidable.

     The “further season” is literally a year-long period between Armageddon and the terminus of the 1,290-day period (Daniel 12:12).  It would appear that the conventional placement of the Battle of Armageddon at the end of the tribulation period is erroneous.  For otherwise, the phrase “a further season” (ELH) or “even for a time” (KJV) would not be present.  We know the total length of this time of great tribulation lasts 1,290 days.  Both phrases indicate a year (or less, possibly).  Logically, then, the Battle must not be the final event.  Indeed, from v14-15 under discussion here, it appears that the Battle of Armageddon must happen within (as opposed to at the end of) the final year of the 1,290-day span.