Tinderbox
This tool has a lot of potential, enormously powerful and complicated, its a great thinking tool, with incredibly powerful exporting options, I think if you played around in this you could prototype a site very quickly and then export the site map as HTML. I warn you though this tool has some annoying idiosyncrasies and makes you do things that feel like work-arounds.
Voodoo pad
its a notepad that acts like a wikki, one of the best tools for hypertexting notes together, you can also drag and drop files and folders onto it and it creates hyperlinks ot them.
DevonThink
Not an outliner or a hyper text tool but it is very good tool for managing tonnes of text documents, indexing them and infering connections between them. More of a search engine for your harddrive.
(all mac os X)
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