Outline Stroke error

Working in CS4 Snow Leopard on an image with a TON of paths. Unable to outline strokes. Receive the following error message: "The operation cannot complete because of an unknown error [%s] Error: 0SEG"
Able to outline strokes on individual paths and small sets of paths, but not larger sets of paths.
Any ideas???
Or... I have a document in all black (with large areas of white fills). I'd like to send only the blacks to Photoshop with the white fills treated as transparency. I'm trying to subtract the whites with Pathfinder, but I can't get my strokes outlined. I've tried printing a color separation but I'm not able to print to - or save - PDF as a document.

I used to use Illustrator every day. I still consider it a favorite program, but I use it sparingly at best. I spent a few gripping hours on the Outline Stroke problem. Once my specific challenge was resolved in CS on Windows XP, though, I moved on. I encountered the same problem a few weeks and a few re-starts later and, again, moved the file to CS in XP. If I didn't have the old version I figure I'd be S.O.L. and in fits of sobbing anger.
Within six months of purchasing CS4, I've reset all of the preferences and moved folders, etc. to address a handful of problems - all to no avail. I suppose I should join the chorus of others on these boards lamenting the quality of CS4 on Snow Leopard. I suppose I should also feel lucky that Illustrator works crappy, because Fireworks won't open at all. Then I should probably feel inadequate among peers, suck it up, and buy a copy of CS5?
Lame answer, I know. Sorry to have more whining and less good info.

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