
Before anything else is said, I am truly convinced that any creative work should start with a sheet of paper and a pencil. By creative, I mean any work where you have to come up with something, well, new. When creating wireframes for an enterprise piece of software that idea is restricted to initial brainstorming sessions and pretty much nothing else since you have to move to a computer for the sake of efficiency. And there is so much more work to be done. And revisited. And refined. And shared. And packaged for the final deliverable. When you add Agile process to the equation (which I think is a win right there) you will revisit your wireframes a lot of times.
Just to paint an example, let’s say we have about 20 wireframe screens. And let’s say that in the course of creating requirements, somewhere towards the middle of the road we decide to change some element in our application header that is repeated over the 20 pages. Ouch! This can be a cumbersome task if you are not using the right software because you would need to make the same change 20 times. Now imagine you have to do it daily because refining and testing the idea is the purpose of creating wireframes in the first place. Did I mention that there might be a lot of wireframes?
Right choice of software for creating wireframes is very important because if one doesn’t think it through, it can balloon the time needed to maintain them by several hundred percent.
I used to create wireframes exclusively in Adobe Illustrator, but on the latest project, I switched to Omnigraffle 5 because there are a number of people working on the wireframes besides me, and I thought that it would provide greater collaboration tools, plus there is the availability of its widely known stencils created by other UXD people.
Before using Omnigraffle, I thought that Illustrator was a good option, but even greater is the combination of the two to take advantage of their strengths.
Stencils
Stencils are also extremely important when you have multiple IA’s on a project because they provide a way to deliver uniform material. However, while you can find a lot of them freely for a lot of different purposes, they may not necessarily support your purpose, which means you’ll need create a new stencil and add it to your Stencil Library.
Drawing vector graphics in Omnigraffle feels like having one hand tied behind my back. My guess is that Omnigraffle is not meant for detailed vector graphic creation.
This is where synergy of Illustrator and OmniGraffle shows the best. Create your symbols/stencils in Illustrator and easily import them into Omnigraffle by first exporting them as PDF from Illustrator. Omnigraffle picks up PDF and retains the vector editing capabilities. That gives me a great sense of relief because with that option I can create my own stencils far detailed and easier and they’ll give a polished edge to my deliverables. In addition, I now have a stencil library the entire team can share so all the wireframe elements are uniform, regardless of who created them.
Single point that a spoiler is that when you update/edit a stencil in Omnigraffle it does not propagate to wireframes where it is already placed – you need to manually swap them. That to me sounds unacceptable for an efficient workflow. Illustrator has Symbols, Flash has a Library of Movies, Flex has components and so on. You edit the object in the library and that change propagates to all the places where the object is placed. I’d really like to see this feature added to OmniGraffle 6.
Shared Layers
Stencils not updating automatically in OmniGraffle is not such a tragedy because of the Shared Layers option.
From OmniGraffle help: You can share a layer between multiple canvases. That way, whenever you change the layer, it affects every canvas that shares that layer.
So you still have to swap out your edited stencil but you need to do it only once vs. 20 times.
Shared Layer concept doesn’t compare one to one to a library of stencils because a shared layer implies shared coordinates too which might turn out to be more that you bargained for.
CONCLUSION
OmniGraffle on its own is a good tool but in my opinion an incomplete one. If you prop it up with Adobe Illustrator, you get a truly good solution. Add a file versioning system and now you can work with a piece of mind . Since OmniGraffle folks seem to be adding nice features in each version I’m already looking forward to the next one.

So, perhaps I was a little over zealous in my earlier comment
)
Are you using CS3 or CS4, and Omni 5 or 5.1?
How specifically should the ai file be exported to PDF, just use the PDF defaults?
And how specifically do you open the PDF in Omni- the article says “Omnigraffle picks up PDF “. Do you just open the PDF file with Omni, or is there a trick?
Thanks for you help,
Theresa
Omnigraffle is a quite popular wireframing tool on Mac OS. I wish I had a Mac to give it try!
FlairBuilder is also an wireframing/prototyping tool that runs on Mac as an Adobe AIR. It supports multi-page wireframes with the option to define masters and attach them to pages as background. Saves a lot of time and it’s pretty simple to use.
Besides that it features greater interactivity, that is on page components behave and feel like real components. Thus FlaiBuilder may also be used for advanced prototyping.
You may give it a quick try online at http://www.flairbuilder.com/demo
Cheers,
Cristian
OmniGraffle Professional 5.2.3 which I’m using now will open a native Illustrator CS4 .ai file and leave you with editable shapes that you can fill.
You can copy and paste the shapes into a new stencil, they appear as Bézier items.