I thought it important to finish my thougths on Luke 16, having posted on 16.1-18 below.
Luke's story of the rich man and Lazarus has sparked much debate regarding issues of the afterlife. Some argue over whether or not the story is a parable. (If so, this is the only one in which Jesus names a player.) This study hopes to look beyond such debates, to find the kernel of Jesus' presentation based on the given textual data.
I have argued elsewhere that Jesus’ teachings found in GLuke implicate the priesthood. I believe this story to be one such instance. Five points demonstrate:
1. The rich man is said to be "clothed in purple and fine linen" (Luke 16.19). This is a description of the high priestly garments, according to Exodus 39.27-29: "The also make the coats, woven of fine linen, for Aaron and his sons, and the turban of fine linen, and the caps of fine linen, and the linen breeches of fine twined linen, and the girdle of fine twined linen and of blue and purple and scarlet stuff, embroidered with needlework; as the Lord had commanded Moses" (see also Leviticus 16.4). The apocryphal book of Sirach says likewise: "[The Lord] clothed [Aaron] in perfect splendor...with the sacred vestment, of gold and violet and purple, the work of an embroiderer" (45.8-11). Josephus notes the same: "[In Alexander's presence] The priests stood clothed with fine linen, and the high priest in purple scarlet clothing..." (Antiquities 11.8.5 ). So, Jesus' description of this rich man matches that of the high priest.
2. In Jesus' story, Lazarus laid "at his [the rich man's] gate" (Luke 16.20). This might very well refer to the gate which guarded the temple. Luke, in Acts 3.2, 10, mentions another beggar at the temple gate, there called Beautiful.
3. Jesus' story may have some close ties to the story told in John 11, in which Jesus raises his friend Lazarus from the dead. First, note the aftermath of the miracle in John 11.47-53. Caiaphas the high priest sought to retaliate against Jesus' raising of Lazarus (11.49ff.). Second, note that Caiaphas was a member of the Sadducees (Acts 5.17). Some of the priests were Sadducees, some were Pharisees (see Acts 23.6). The Sadducees denied the resurrection of the dead, angels, and the spirit (Acts 23.8). Jesus' story in Luke 16 includes all three of these elements: allusion to Lazarus' resurrection, angels carrying Lazarus' body away, and several conscious figures after death. Jesus used this data to create an ironic story to show the priesthood's corruption. Luke’s ironic story then is perhaps a creative telling of John’s history.
4. The rich man in Jesus' story is said to have five brothers (Luke 16.27-28). It has been argued both here at this blog and at Richard Anderson’s blog that Luke wrote to Theophilus the high priest of 37-41 CE. This Theophilus had four brothers (Mattathias, Annanas, Johnathan, and Eliezer), one brother-in-law (Caiaphas), and a father (Annas) who each served as high priest in the first century. If Jesus was exposing the priesthood in his story, which is perhaps an ironic presentation of the raising of Lazarus (as told in John 11), then Caiaphas would have been the rich man in Luke 16. For he had five brothers[-in-law].
If all of this be true, note the irony of Jesus’ tale: Caiaphas the Sadducean high priest, who denied the resurrection from the dead, angels, and the spirit, begged father Abraham to raise Lazarus from the dead and send him as a witness to his family, to warn them of the coming judgment. Abraham's reply: "If they do not hear Moses and the prophets [which they surely knew well], neither will they be convinced if someone should rise from the dead [emphasis added]."
Perhaps the greater irony: Jesus DID raise Lazarus from the dead! It was that fact that Caiaphas scoffed (John 11.49ff.).
 I have briefly studied the terms for “gate” as they appear in Luke’s writings, as well as other literature. I did not find anything which seemed significant to my case here. Further study may prove otherwise, in which case I’ll modify this point.
Regarding the high priestly garments:James VanderKam, scholar of Hebrew scriptures, writes: “During the period when the Romans assumed control of Judea, the governor took over [the high priestly garments] and permitted the high priest to have them only during festivals” (An Introduction to Early Judaism, 180). After Herod died, the garments were in the custody of Tiberius (14-37 CE). Then, as a favor, Vitellius (governor of Syria) gave the people back the garments. They remained in Jewish control until the death of Agrippa 1 in 44 CE. When Rome tried to reclaim the garments, the Jewish people sent a delegation to Rome and were apparently granted custody.
VanderKam concludes, “The garment was thought to convey such a powerful impression that the authorities worried about the political and social effect it might have” (181). The apocryphal Sirach 45.6-13 and chapter 50 indicate that the garments bestowed great splendor upon the high priest, Simon at the time (50.11; see also Wisdom of Solomon 18.24). Philo suggests that the garments had cosmic symbolism (Life of Moses, 2.109-126, esp. 2.117ff.). Josephus also gives an elaborate description of the garments (War, 5.6.7 [231-36]). Indeed, he says the high priest was the "captain of [Israel's] salvation" (War, 4.5.2 ).
If it is true that these garments bestowed such glory and (political) power upon the high priest, perhaps their absence helps explain why temple-defiant groups emerged. Theophilus, high priest of 37-41 CE, would have been the first in some time to have enjoyed the priestly glory of old. (His father, Annas, high priest of 8-15 CE, would have been the last to wear the garments before Theophilus.)