@Geoff - To my surprise, the YouTube embeds were actually playable videos from YouTube. I thought they would just be screencaps. But the videos had nothing to do with the content they were displayed under.

@Dougal Campbell - That's what I was thinking. One of the biggest problems is relevancy and context which is a problem already solved for them considering they already know the most trafficked sites that talk about specific subjects. All they would need is a good sales/marketing team that could purchase the context relevant advertising to display on those sites. Then again, perhaps Automattic really has no interest in pursuing that route and that's why they've decided to partner up with Federated Media instead.