That question has two possible meanings 1) was Jay's form of enslavement a good thing, so that it would have been just fine for him and others to continue to do it indefinitely? Did his form of slavery stop slavery from being evil? The answer to that is clearly "No". 2) Given that Slavery was and always must be an evil, was this the best possible way for an affluent and free person to live in the same century with that evil? Would it have been better for him to have isloated it himself from it, instead of to some degree collaborating with it in hopes of making it somewhat less evil? Did he suceed in making it less evil for the people he enslaved? The answer to that question is to some degree buried in the details.

Here's a similar example. I will assume we agree that female genital mutilation is evil. Part of the reason it is evil is that it is often done in unsanitary conditions, producing sepsis and death. It would be less evil if it were done in a sanitary hospital. Does this mean that Doctors should perform those mutilations to decrease the infections. I would say "hell, no!" Was Jay's form of slavery sort of like this? Maybe, I'm not sure.