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I find the styles process baffling also. I have had to select whole documents and unset everything then rebuild my headings et al because I have become lost in "what is applied where and why does this section look like that!"
That sounds too familiar to me. Now, I am not an experienced OO user, but I find myself often in the situation where it seems the easiest ways to remove all styles and start all over - which is tedious. Omni might want to try to do something for the more casual users here, or: try to get better introductory documentation, as discussed in a thread in the OmniGraffle forums (I think its called "OmniGraffle the definitive guide")