Zhuangzi doesn’t teach detachment. His recommended way of living looks like detachment, but it’s actually a radical reorientation of your relationship to your personal values and the world around you. That mode of living still allows for attachment. Zhuangzi still mourned the death of Huizi, after all. The detachment you seem to be talking about is Buddhist influence on later religious Daoism (道教 as opposed to 道家).

That being said, I am sympathetic to your point and I think you’re right. I’m only pointing out some blurring that you have between religious Daoism and philosophical Daoism, which are distinct branches of thought. It’s easy to fall into this trap if you follow online Daoist groups instead of studying Daoism academically.

> Where would that put Hitler or Stalin? Certainly there must be a point of no return?

No. To Zhuangzi, right and wrong are problematic concepts that we can never be certain of. We create wrong by saying that something is right. The wrong thing never existed before we said that something was right. We created a philosophical problem where there was none originally.

> On a more modern stance, consumerism has driven unethical business practices. Perhaps that has helped the modern world advance in many ways… but does that mean a slave runner is off the hook in the long run? So they shouldn’t care about another living creature “for the greater good” since they feel right about who they are?

This is all in line with ethical thinking. Zhuangzi rejects ethical thinking. You’re assuming that some business practices are ethical and unethical and that slavery is wrong. Zhuangzi would say that’s not necessarily the case.

> Again where’s the line? We’ve seen plenty of grifters and nasty dictators (e.g. Rush Limbaugh, Leopold II) pass away peacefully and with honors. Why would they care about the world if they didn’t before? If I commit atrocities and die thinking the world will love me for it.. then what else matters?

The point is not to care about the world. Daoism is a personal cultivation tool. It’s not world oriented, it’s self oriented. In its historical context, the Zhuangzi was radically anti-political.

> It’s a perfect world philosophy that I wish we could live in but realistically that’s just not the case.

You’re expecting the wrong thing. Zhuangist Daoism is specifically for a world that’s not ideal or perfect. It’s a way to deal with the horrors of a war-torn world in a healthy way. When Zhuangzi was writing, the world was in a far worse state than ours. He was trying to find a way out.

Not even close. Unless you’re an undergrad or not even in academic philosophy.