I think I did address your question...

I think you let the audience take from it what they will. If you want to prompt them to think about it a little more deeply than they might, introduce it, if you like, with a question for them to ponder. Or share your own questions about it, VERY briefly, as if to say, "What was he THINKING?"

It's not so hard to think about a slave loving their masters while also hating their living situation..... you could think of it as a protracted Stockholm Syndrome, as with hostages who bond with the only authority figures present for various reasons that defy logic. Or you could see it as a triumph of the human heart, to be able to love in those circumstances. Or it could be the song of a black person who wants to curry favor with white listeners. Or there could be almost any "true" explanation of the song and its many layers of meaning at the time it was created.

But my point is (and was), it's NOW. People will take from it what you try to convey, and what they can grasp from within their own perspective, now. That's the job of most of us here, unless we are trying to sell ourselves as historic re-enactors teaching with song.

Personally, I like the idea that here's this black person looking forward to Massa being planted, a symbol of total power now nicely reduced to wormbait.... that the old South he's singing about includes not a living Massa, but a dead one... that the singer and his family will be together in death (maybe even heaven), while knowing that Massa also is gone, gone, very gone (and maybe NOT in heaven). But then I'm a little warped.

~Susan