Automagic Annotation Stencil
 

I couldn't stand wasting any more time manually updating annotations on my wireframes, so I made the attached stencil. Inside the archive is also example doc. It takes the "meta data" associated with each label and makes a nice, ordered outline list of each label and its data. You know, like you've always spent hours doing manually and then cursing clients when they want you to change something that seems oh-so-simple but is sooo not!

Use the labels as directed and click the Big, Friendly Button to see it do something every UI designer working in OmniGraffle has been longing for. She's a funky little AppleScript that makes this all happen. I've tested it pretty well, but there's always room for error.

Hope it improves your relationship with OmniGraffle as much as it has mine. Apologies if you thought it sucked beyond belief. They can't all be winners.