This is a great debate and some good comments all around, but I do think it's important to keep in mind that Matt's statements were from 2005 and 2009, and even the 2009 wording was a bit more nuanced. I strongly suspect Google has eased up on this early technical constraint. For example, try a search for "shop ipad" - you'll see this Apple.com URL in the Top 10:
store.apple.com/us/browse/home/shop_ipad/family/ipad/select
Google seems to have no trouble bolding "shop_ipad" as two words.
I still completely agree that, if you were starting fresh, I'd go with hyphens. A sitewide 301-redirect does carry some risk, though, so I think it boils down to this - are your pages ranking now for terms in the URL? If they seem to be ranking and it's just a matter of ranking better, I doubt the change would help much. If they seem to not be ranking at all and you suspect the URL terms are to blame, that's a different story.
Even in a perfect world, keywords in the URL are just one, relatively small factor. I'd want to see the data, but my gut reaction is to leave it alone until you need to make a sitewide URL change for other reasons.