Here’s something I wrote a while back on the parallel passage from Matthew:
Matthew 10:15 and 11:23-24 read:
“Truly, I say to you, it will be more bearable on the day of judgment for the land of Sodom and Gomorrah than for that town…And you, Capernaum, will you be exalted to heaven? You will be brought down to Hades. For, if the mighty works done in you had been done in Sodom, it would have remained until this day. But I tell you that it will be more tolerable on the day of judgment for the land of Sodom than for you.”
First, it should be noted that Christ is not here contrasting the punishment of Sodom with a punishment that all the wicked will receive the end of time, in another state of existence. He’s contrasting the punishment of Sodom with the punishment of those cities which rejected the ministry of he and the apostles. Now, the rest of Scripture is utterly silent with regards to a future judgment for Sodom, Tyre and Sidon. In Genesis 19 and Isaiah 23, we find a very particular account of the judgments of these cities, but not a word is said of their ever being judged again at another time. Christ is here simply speaking of the day in history when God’s vengeance would fall upon the cities in view that were guilty of rejecting him. The judgment is in this world, not in “eternity.”
It may be argued that the future tense Christ uses in reference to Sodom and Gomorrah (“it will be”) disproves this idea, and extends the judgment of all the cities of which Christ speaks into a yet-future time. However, in Ezekiel 16:46-56, the prophet figuratively represents Samaria as dwelling at the left hand of Jerusalem, and Sodom at its right. This was not literally true, however; both cities had been destroyed for centuries. But Ezekiel is speaking AS IF they were then dwelling alongside Jerusalem, in order to more forcibly impress upon his reader’s minds the contrast he’s making between these cities and that of the present, wicked state of Israel. If Ezekiel could use the present tense when speaking of Samaria and Sodom, and thus represent them as being in existence at that time (when, in reality, they had been destroyed ages ago), then Christ could certainly speak in a similar way, in reference to a similar situation! He is simply speaking AS IF Sodom (and other cities) would be present at the time of the judgment of the then-present-day cities of Chorazin, Bethsaida and Capernaum to be judged alongside them, in order to more forcibly impress upon the minds of his listeners the greater severity with which these Jewish cities would be judged.
Moreover, Christ is explicitly speaking of a judgment upon cities, not just the former inhabitants of cities. Christ does not say, “…more tolerable for those who were the sinful citizens of Sodom.” No, he says, “more tolerable for the land of Sodom” (Matt 11:24), and even says Sodom “would have remained until this day” (v. 23) implying that, in his day, it was no more (and, as a city, would be no more). This to me is proof positive that Christ does not have in view a second, future judgment of all the individual people who once lived in this city (or any other city). He’s talking about the cities themselves (in the case of Sodom, he’s referring to that which “would have remained” until that day) as they existed and functioned in their former geo-political capacities and locations. Thus, Christ is not saying that “the land of Sodom” has another “day of judgment” in the future, because the land of Sodom was judged long ago, and the city doesn’t exist anymore (again, v. 23).
Even if God were to resurrect every former citizen of this city and the others, the cities themselves would not be resurrected, with their original location and corporate capacities. The cities would still be no more. At the resurrection of the dead there will be no “Sodom and Gomorrah,” only those who were once citizens of these cities. Thus, even if there is to be a future judgment in store for all individuals (though scripture does not teach this), there is no more “Sodom and Gomorrah” left to be judged. Any judgment upon a city must be experienced on the earth, while the city still has its metropolitan existence. This temporal world is the only place where cities like Sodom and Gomorrah have such an identity and existence, and thus it is only in this temporal world that cities can be judged as such.
But what is meant by the expression, “exalted to heaven?” It doesn’t mean “to go to heaven after death.” This is simply an expression to denote great privileges. Capernaum was quite prosperous, being successful in commerce. But most of all, it was signally favored by the presence, preaching, and miracles of Christ! He evidently spent a large part of his time here in the early part of his ministry, and in Capernaum and its neighborhood he performed many miracles. And the words, “brought down to Hades” doesn’t mean that all the people would go to a place of torment (either after death or at some future time), but that the city which had flourished so prosperously would lose its prosperity, and occupy the lowest place among cities. The word “Hades” literally denotes the domain of death and the grave, and here figuratively denotes the inevitable state of desolation and destruction to which Capernaum would be brought as a city (and thus stands in stark contrast with their being “exalted to heaven”). All of their privileges, honors, wealth, etc., were to be taken away, and they would sink as low among cities as they had before being “exalted.” This was literally fulfilled. During the Jewish-Roman wars (less than 40 years from the time Jesus uttered these words), Chorazin, Bethsaida and Capernaum were so completely desolated that it is difficult to determine their former locations.
Thus, the “day of judgment” for Sodom and Gomorrah, Tyre and Sidon, Chorazin, Bethsaida, and Capernaum, was when these cities were destroyed in this world. Notice that all the punishment threatened against Capernaum is set forth in the expression, “will be brought down to Hades.” Again, “Hades” does not denote judgment in a future state, but the domain of death (and in this context, desolation and destruction in this world). And as Capernaum was equally guilty with the other cities mentioned (and even more guilty than cities such as Sodom), it makes no sense at all to understand its punishment as being temporal, and the others as being in a future state. No more is expressed by the phrase, “more tolerable in a day of judgment” than in the phrase “brought down to Hades.” Christ is simply contrasting the severity of temporal judgments upon cities and their citizens. As the spiritual advantages given to Capernaum had been greater, so its punishment would be more severe on the “day of judgment.”
But like the doctrine of hell, I’ve just come to see the Scriptural evidence against it as being more compelling than the evidence for it (but I’ll take a belief in “life outside the body” over the doctrine of hell anyday 
). Anyway, I plan on addressing the rest of your comments a little later, when I have some more time.
