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You can do a bit of this already. In the print command, select "Layout" in the options, then set the number of pages per sheet to 2. You'll get two pages of your outline printed side by side on each sheet, oriented in landscape mode.

Here's what the dialog looks like in 10.4.11:



And a preview of the result:



Unfortunately, I haven't found a way to go to more than 2 "columns" per page, as many lists would permit.

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