If Facebook advertising is so clever, how come it acts so dumb?

Writing in the latest edition of Vanity Fair, Kurt Eichenwald states that Facebook has "quietly been pioneering a marketing business model unlike any other" and goes on to praise the social networking Goliath for developing new targeting techniques that give "advertisers an unprecedented ability to reach only the potential audiences they want". Eichenwald comes to this conclusion, he says, following months of interviews with Facebook advertising clients, investors and key executives from Facebook itself. The picture painted by Eichenwald in Vanity Fair is of a business which has pretty much revolutionised the marketing and advertising space online, and reinvented itself as a result. He talks of the kind of insight that Facebook can deliver to advertisers in order to enable them to deliver highly targeted messages at just the right time, such as tracking down "potential buyers at any point along the purchasing path" with an example used of Facebook users having checked travel prices without completing an order being able to be hit with ads "urging them to pull the trigger on buying". It all sounds, from the advertising executive perspective at least, like marketing heaven. So why do I feel like I am in some kind of perpetual Facebook advertising hell instead?