David Resnick asks for strategies that have been used for explaining the Torah's toleration of slavery in the day school classroom. There are two sources that come to mind that can be helpful (I've used one them, I hope successfully) by providing a parallel approach in a different area:
One is the Rambam's explanation of animal sacrifice in the Moreh Nevuchim 3:32, where he argues that God will command an inferior form of worship if it has more pragmatic value than the superior one. Ideally worship would be through meditation or prayer, but the generation of Egyptian slaves were on a level that was more used to animal sacrifice as the main mode of worship, so the Torah made a concession to their cultural norm. But the hope is that people will eventually come to understand that prayer and meditation are superior to animal sacrifice. One could parallel this passage to slavery, arguing that the Torah's toleration is a concession to the cultural needs of the time, with hopes that eventually people will see freedom as superior. (Note that the inferiority of sacrifices is not a moral one in the Rambam, but aesthetic and intellectual, whereas we consider slavery as morally inferior to freedom. But it's still parallel.)
The second (and the one I used) is the collection of Rav Kook's writings on vegetarianism called "Chazon Hatzimchonut". There Rav Kook argues that eating meat is morally problematic, which is why the Torah prohibited it in Eden, yet eventually the Torah allowed it when Men started killing each other. Better that men work on person-to-person morality first, and save person-to-animal morality for the end of days when people are at peace. Were the Torah to insist on person-to-animal morality in the present day, people would continue to kill each other and quiet their conscience by being kind to animals (as the Nazis did, although Rav Kook didn't live to see his bold prediction come true). Rav Kook argues that the mitzvot of Kashrut are like little windows to the future ideal of person-to-animal morality. By dropping hints through mitzvot like ritual slaughter, allowing us to cultivate and consume only vegetarian animals, and others, the Torah hopes to eventually move the Jews and mankind to realize that eating animals is altogether wrong. Still, we must maintain our priorities and avoid banning eating meat too early or person-to-person morality will take a backseat.
When I taught Rav Kook I used slavery as parallel example of an ideal that people were not ready for, but the Torah gave mitzvot about how to treat slaves in order to gently nudge the people to eventually realize that slavery is wrong. I also suggested that this may actually have worked historically. The argument can be made that the Torah's insistence on all men being created in God's image, along with the regular admonitions to be kind to the stranger in light of our own suffering in Egypt, were major forces behind the eventual acceptance by the civilized world of the immorality of slavery. Let's not forget that a major story in the Torah is the freeing of slaves, and that many slave songs from the US were inspired by that story. And that the decision to free slaves was based on the notion that all men were created equal, a notion that came from the Bible. The Liberty Bell, after all, has written upon it the verse from Vayikra calling for the freeing of slaves. This is a suggestion, but it does enter into a history lesson that I'm not so qualified to give.
Best Regards,
Mark Smilowitz
YTA High School for Girls
Jerusalem, Israel