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I realise that this is not exactly what you ask for. However, you do need to appreciate that (a) OmniGraffle developed and matured as a drawing tool in its own right, separate from other programs, and (b) there is a Apple- intuitive or OG way to do exactly what you want (but not in the exact same sequence of steps you request or that another program does).

You need to learn the Tool. You do the operation in Illustrator using Illustrator facilities; you do the same operation in OG using OG facilities; expecting either tool to operate like the other may not be a good idea.

1 Go to the Style:Summary Inspector
• read up on it (the manual is short and sweet; very good run-through at the beginning; can be downloaded), and play with it
• use the "wells" to pick up and paste the style-set you want onto an object
• get used to the method for copying Style-set from one object and pasting it to another object

2 Go to the Toolbar:StyleBrush
• read up on it, and play with it
• Learn the distinction between:
• a Tool chosen to operate once (one click)
• a Tool chosen to operate multiple times (two clicks) until it is cancelled
• the little down-arrow on the Tool icon (eg. ClearContents)
• get used to the method for copying Style-set from one object and pasting it to another object

3 Let's say you have proliferated an object 10 times. Whether it is on the same canvas or not, visible or not, matters, but now for now. Go to Canvas:Select Inspector
• choose your setting in the SortUsingStyles drop-down (you only need to do this once)
• choose your 10 objects by clicking, shift-clicking or command-clicking (not by selecting the objects on the canvas). Yes, because the 10 objects are not now the same, you will pick at least two Selections
• apply the Style-set you want, from either [1] or [2]
• often that will now make the 10 objects one Selection

Cheers