IMO the fundamental difficulty is that anarchism is framed in terms of a negative - the absence of hierarchy. This makes it a fantastic foundation for critiquin

IMO the fundamental difficulty is that anarchism is framed in terms of a negative - the absence of hierarchy. This makes it a fantastic foundation for critiquing existing (power) structures on their own merits in isolation. But that foundation makes proposing new structures a secondary concern. So then you get the various schools, each trying to describe how they themselves think society should be positively structured, while awkwardly trying to avoid the fact they're proposing new structure, and all the ways that can (and likely will) go wrong. The problem gets especially poignant when trying to push existing society in one of these specific directions, where undermining some power structures can cause others to fill the vacuum. You'll also find yourself in opposition to other groups pushing for their own freedom, but focused on a different part of the existing power structure that makes the most sense for them to start with. My own synthesis is something along the lines of anarchism without adjectives where we need to be against immediate oppression of individuals by power structures, but also realizing that scaling any such movements will inevitably spawn their own oppressive hierarchies, likely aimed at people different than us. Ultimately I think the larger societal changes in individual freedom are created by new technologies, each of which can either support or oppress individual freedom.