It seems to me that there are two main points which Kyle martials to his cause. His first is that if many are damned, then God's will has been frustrated, and unless we are prepared to think God a failure, we can't think that many are damned:
If you say, as much of Christianity does, that God created the universe and specifically human beings–creatures made in his image and likeness–for the purpose of participation in the love life that is God, and you also say that most people will refuse this destiny, then logically you’re led to say that, overall, creation won’t achieve its purpose. Overall, it is a failure. Overall, the purpose for which God created goes unrealized. Overall, God’s desire and will are not done. This would seem to make God, as Creator, something of a failure, even if you can, through some dexterous theodicy, get God off the hook for the damning decisions of his hellbound creatures.This is, as I recall, a complaint that many of the leaders of the Protestant Reformation (or Revolt, if you prefer) were big on. If we allow that God created each of us with the purpose of knowing, loving and serving Him and being united with Him forever in heaven, and if we also allow that in sin we may reject God and separate ourselves eternally for Him, then by this line of thinking man may defy the will of God and frustrate His providence, and God is thus not all powerful. The most extreme solution for this is to claim that God actually intends some people to be damned (predestination) and that He crated them for this purpose. Thus, God's will is never violated since He wanted those souls damned anyway.
Kyle, of course, being a less dour fellow, is taking things in the opposite direction: God doesn't want us to be damned, and we can't believe that God's will isn't accomplished, so obviously none (or few) go to hell. It seems to me that either course essentially assumes that God doesn't will humans to really have free will. If we believe that God really wills us to have free will, then it by no means follows that if people use that free will to reject God that His creation is a "failure".
The second point Kyle makes relates to whether anyone ever really chooses to reject God:
From my own place, the doctrine that many are doomed to fire and brimstone and endless replays of One Direction hits just makes no sense. My own senses lead me to deny the observation of Fr. Longenecker that “every verifiable bit of evidence from history and yesterday’s newspaper reveal the total depravity of many men’s hearts and their spitting hatred of all that is beautiful, good and true.” I can’t think of one person who, in total depravity and rightness of mind, hates all that is beautiful, good, and true. Not one. Even the worst of sinners are motivated by something they value. That many people’s hearts are totally depraved and hateful of every swell thing just doesn’t correspond to reality.This, it seems to me, is the more key question. Kyle wrote similarly here a little while back:
I know people who sin, of course, and do so knowing it's wrong, but none of them mean to put themselves above God or in opposition to him, as if that's their motivation. Either they justify it or presume God's mercy, in which case they would seem to have a lack of full knowledge, or they have fallen due in part to their weakness, which would suggest a lack of full consent. You're describing moral sin in such a way that very few people are really guilty of it. That sounds nice, but it doesn't sound like what the church says, certainly not the traditional idea that few will be saved and many will be damned.Once again I'm reminded of a someone more dour version of the same concern: one of my friends I used to debate religious issues with as the teenager was always insisting that no act was really good because no one was ever totally motivated by "the good" and not by other more practical or selfish concerns. It seems to me that Kyle is, in a somewhat similar manner, arguing that no act is ever a total rejection of God because we always act with some other object in mind as well, in addition to the knowledge (assuming we have that knowledge) that we are acting contrary to God's will.
There's a sense in which I would agree with this. During this life, no rejection of God is total, since we still have the chance to repent. Our experience of God in this life is not direct and total, and our rejection of Him in this life is, likewise, not yet total. That is why (contra one of Dante's innovations) we cannot be damned until the individual judgment, after death.
However, we do reject God often -- sometimes more gravely than others, sometimes more knowingly than others. We do this whenever we put our own will above God's and choose to do what we want rather than what we know to be God's will, what we know to be good.
As Kyle points out, we invariably do this with some sort of proximate good in mind. Our goal is not simply to offend God or to reject good, but to achieve something or other that we think of as a good -- that is, "a good" in the sense of some thing which we desire. Even if I do something out of sheer orneriness (say, someone I dislike asks me to do A, and so I choose to refuse to do A simply to defy that person) I am still seeking a good of sorts in that I'm seeking some (perhaps illusory) sense of satisfaction in commanding my own actions.
The thing to keep in mind, however, is that when we set our own will above God's and seek "goods" other than that which is good, we reject God even if that is not our sole object. If I defraud Kyle, I may at a certain level do so in order to achieve the "good" of absconding with the riches produced by his philosophical blockbuster, but at the same I am choosing to put my will (to take what I want) above God's will (which tells me "Thou shalt not steal.")
If I make a life of defrauding people, I build for myself a warped understanding of the good. The more I live by that warped conception of the good, the more I train myself to reject the true good which is God's will.
This is the sense in which people often describe all sin as being at root idolatry. Even if I tell myself "I'm just weak" or "I'm counting on God's mercy" or "I don't agree with God on this one", when I form a habit of choosing my will over God's will, I form a habit of rejecting God and putting myself in isolation from Him.
I think it's not a bad image to look on the individual judgment in terms of a final choice to either embrace or reject God, however it's important to see that decision in the right terms. This is not a simple question of "would you like everlasting happiness or unhappiness?" in which every person would obviously have the same answer. After all, we know that Lucifer, one of the chief among God's angels, rejected God utterly. Why? Did he simply get fed up with happiness and decide he wanted to suffer instead? No. To the soul which refuses to embrace God's will, union with God is no happiness. Isolation may be suffering, but it is a suffering chosen because to the rebellious will union with God is suffering too. When we build the habit of putting our own wills above God's, as we wrap those decisions in price or self-definition, we turn ourselves into the sort of people who would find it very painful to embrace God's will totally. Perhaps I simply have a much darker view of humanity than Kyle, but I find it quite believable that someone would rather reject God than reject all the actions and beliefs which he holds in opposition to God. Sometimes people even state things in exactly those terms.