To me it seems that in the end main measure is how deep/powerful are hierarchies in a system. How much power has one individual over the other.

Many libertarians and liberals believe that it's the freedoms one has that make system anti hierarchical.

But as you point out when you have absolute freedom in market based society then you eventually end up with intensely deep hierarchies.

In other words you are free to do everything but there is no guarantee you can do anything - even the most basic things like get food or shelter. And most end up with the short side of the stick.