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Hi Nat,

I agree with Mitchell - the need you're describing sounds like it would be better met by OmniFocus. That said, I find almost endless uses for OmniOutliner.

I have one outline for each project I'm working on, to keep research, thoughts, related materials, drafts, etc.

If I'm hiring, it's where I keep lists of positions to be filled, indented under that is an item for each applicant, indented under each applicant is their resume and notes about them.

I've got outlines for planning trips - where I can store destinations, with sub-items for each including hotels, photos, restaurants, maps, etc.

I've got an outline for family history research (which I like much more than the commercial genealogy software).

I recently thought about buying a telescope. So I made a quick outline to store all the different articles (explaining what an amateur like me needs to know before buying), photos, and examples of different telescopes from various shopping sites. So the outline includes text, web pages, photos, a variety of data. The outline provides me a really easy way to keep all this information together and easily viewable.

All told, I really the outlining metaphor for pretty much anything I get interested in that involves collecting information. I find it easier to store and categorize information of all kinds than putting files into folders - it's also easier to see everything at once, compared to opening different files and arranging them around the screen. I just create hierarchies in the outline, and use Expand All or Collapse All to show everything and then easily fold them up and out of sight.

Other people like Evernote for this sort of thing. I like Evernote, too, but for anything I'm actively working on, I keep it all in an outline, as I've found it much easier to work on, and MUCH easier to see everything at once.

Of course, your mileage may vary.