Since writing this post, I have been able to learn more about the transition to Rome in Daniel 11. The relevant impact of that information shows up in two of my more recent posts:
Daniel 11:16 (September 17, 2018)
Testing Daniel 11:16-22 (August 30, 2018).
For the entire chapter laid out with the pronouns identified, you may be interested in the book, Daniel and Revelation Bound Together, available at BibleProphecyCentral.com.
Bible prophecy is history foretold. In no chapter of the Bible is more history detailed than in Daniel 11, written around 535 B.C.
There has been over the years a lot of interest in identifying the kings of the north and south in Daniel 11. But much of the chapter, though not explicitly labeled as such, actually focuses on a third compass point: the West. The spotlight of prophecy moves to the west in 64 B.C. when Syria becomes a province of Rome. And not until the time of the end does the chapter shift its attention back to the kings of the north and south.
The section on the West is reproduced below with my attempt at identifying the players. I've replaced pronouns with the names (in bold) of those most likely referenced, and I've added a few bracketed comments.
16 But Pompey, that cometh against Antiochus XIII Asiaticus, shall do according to his own will, and none shall stand before him: and he shall stand in the glorious land, which by his hand shall be consumed.
17 Julius Caesar shall also set his face to enter with the strength of Alexander’s whole kingdom, and upright ones with him; thus shall Caesar do: and he shall give him the daughter of women [Cleopatra], corrupting her: but she shall not stand on his side, neither be for him.
18 After this shall Caesar turn his face unto the isles [Pontus, North Africa, and Hispania], and shall take many: but a prince for his own behalf shall cause the reproach offered by him to cease; without his own reproach he shall cause it to turn upon him.
19 Then Caesar shall turn his face toward the fort of his own land: but he shall stumble and fall, and not be found.
20 Then shall stand up in Caesar’s estate a raiser of taxes [Augustus] in the glory of the kingdom: but within few days he shall be destroyed, neither in anger, nor in battle.
21 And in Augustus’ estate shall stand up a vile person [Tiberius], to whom they shall not give the honour of the kingdom: but he shall come in peaceably, and obtain the kingdom by flatteries.
22 And with the arms of a flood shall they be overflown from before him, and shall be broken; yea, also the prince of the covenant [Jesus].
[This literary climax mirrors Gabriel’s earlier commentaries that culminated with “the Prince of princes” in Chapter 8 and “the Messiah the Prince” in Chapter 9. At this juncture, before continuing with the narrative, the angel backs up to give us a little more background.]
23 And after the [161 B.C. Jewish] league made with the Roman Senate, the Republic shall work deceitfully: for he shall come up, and shall become strong with a small people.
24 He shall enter peaceably even upon the fattest places of the province; and he shall do that which his fathers have not done, nor his fathers' fathers; he shall scatter among them the prey, and spoil, and riches: yea, and the emperor shall forecast his devices against [or from] the strong holds [Rome], even for a time [that is, one prophetic "year" of 360 prophetic "days" (literal years) extending from the decisive battle of Actium in 31 B.C. (verse 25) to the founding of Constantinople in A.D. 330 (verse 29)].
25 And Octavian shall stir up his power and his courage against the king of the south [Mark Antony] with a great army; and the king of the south shall be stirred up to battle with a very great and mighty army; but he shall not stand: for they shall forecast devices against him.
26 Yea, they that feed of the portion of Mark Antony’s meat shall destroy him, and his army shall overflow: and many shall fall down slain.
27 And both these kings' hearts shall be to do mischief, and they shall speak lies at one table; but it shall not prosper: for yet the end shall be at the time appointed.
28 Then shall Octavian return into his land with great riches; and Nero’s heart shall be against the holy covenant; and Vespasian, and his son Titus, shall do exploits, and return to his own land.
29 At the time appointed Constantine shall return, and come toward the south; but it shall not be as the former, or as the latter.
30 For the ships of Chittim [suggestive of the Vandal naval attacks, a reference to the barbarian invasions as a whole, the first major blow being the Gothic victory over the Romans at Adrianople] shall come against Valens: therefore Theodosius shall be grieved, and return, and have indignation against the holy covenant [the pure gospel]: so shall Theodosius do; he shall even return, and have intelligence with the bishops that forsake the holy covenant.
[After the fall of the Roman Empire in the west, the prophetic narrative continues with the leading western rulers.]
31 And arms shall stand on Clovis’ part, and his army shall pollute the sanctuary of strength, and shall take away the daily sacrifice, and they shall place the abomination that maketh desolate.
32 And such [the pontiffs] as do wickedly against the covenant shall Pepin, Charlemagne, and their successors corrupt by flatteries: but the people that do know their God shall be strong, and do exploits.
33 And they that understand among the people shall instruct many: yet they shall fall by the sword, and by flame, by captivity, and by spoil, many days.
34 Now when they shall fall, they shall be holpen with a little help: but many shall cleave to them with flatteries.
35 And some of them of understanding shall fall, to try them, and to purge, and to make them white, even to the time of the end: because it is yet for a time appointed.
36 And the king [Louis XIV] shall do according to his will; and he shall exalt himself, and magnify himself above every god, and shall speak marvellous things against the God of gods, and shall prosper till the indignation be accomplished: for that that is determined shall be done.
37 Neither shall he regard the God of his fathers, nor the desire of women, nor regard any god: for he shall magnify himself above all.
38 But in his estate shall he honour the God of forces: and a god whom his fathers knew not shall he honour with gold, and silver, and with precious stones, and pleasant things.
39 Thus shall he do in the most strong holds with a strange god, whom he shall acknowledge and increase with glory: and he shall cause them to rule over many, and shall divide the land for gain.