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Thanks in part to this thread, I finally decided to move full-time to TaskPaper. I was already using TaskPaper extensively on my iPad and iPod touch, benefitting greatly from the seamless sync and web service. But since it's now clear to me that OmniOutliner isn't going to give me what I want in the near-to-midrange future, I also decided to switch to TaskPaper for Mac.
It's been nice using OO all this time (since 2001). But now it's time to move on.

Catch y'all later!