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I think this is a prime example of someone not having ever had the functionality not being immediately able to see how it's useful, but once you've had it, you'd never want to be without it.
Example 1. I'm in Publisher (which is actually quite a respectable simple vector layout package, but I digress) and I go Insert / Picture / From File... and the Open dialog appears. I navigate to the folder where the image I want is, and then suddenly remember I needed to touch the image up in Photoshop before I place it into Publisher. So I right-click and choose Open With... Photoshop. I touch it up, save it, and Alt-Tab back to my File Open dialog, pick the newly edited file, and click Open. If I didn't have that facility, I'd have to open Photoshop, navigate to the folder, edit, go back, etc... meaning TWO navigations rather than one.
Example 2. I'm attaching a PDF to a mail message so I've got the Open dialog up, but I can't remember which is the right one. So I right-click and choose Open With... Acrobat to check. Same result -- one navigation instead of two.
Example 3. Insert / Picture / From File..., and I realise I want to create a text file for notes in that folder, so I right-click, New, Text File... and then right-click the new text file and Open With... Textpad.
Example 4. (good grief man, get on with it). Any File / Open dialog, and right-click a file, Copy, then Paste, to create a copy, rename it with a single-click, then open the copy.
You get the picture.
In practice I use this or some variation of it fairly infrequently compared to the number of times I use File / Open (etc) *without* using it, but it's still perhaps 5 or 10 times per work day. So it's hardly a drastic timesaver, especially once I'm quicker at navigating around Finder, but it'd still be very nice -- I badly miss it.
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