[whiletruefork]

I agree that Reddit is taking a naive view on Advertising. There is a huge amount of value to be added here, both to Reddit and the Community by an effective Advertising platform. I'll speak with examples:

r/gaming, a post about Borderlands2 with a sponsored ad that links to one-click checkout on Steam.

r/politics A post about Romney's many lies featuring a donate to Obama link, or vice versa.

r/fitness Featuring a sponsored Ad to a local crossfit gym that is having a free trial.

To pull this off they need much better Advertiser control, sentiment analysis of posts, and inclusion into a larger Ad Exchange (or offer Reddit inventory via an exchange model).