Dana really didn't do anything out of the ordinary in this whole sequence. There are many better examples of hypocrisy out there if someone wants to make a GOOD Dana-hating video.
1. He said that Kimbo sucks as an MMA fighter - TRUE, though he has slightly improved recently
2. He said that Kimbo could only get into the UFC via TUF - TRUE
3. He said that Kimbo would lose in TUF - TRUE
4. He said that we would see if Kimbo was just a fighter or an MMA fighter - TRUE, and he was just a fighter as Dana originally said
He did hedge his bets a little when hyping Kimbo by emphasizing that he is "a fighter", but that is little more than a different way of saying "he tries hard". I would have much less respect for Dana if he said "These guys both suck, so let's watch and see who sucks less today". He is a promoter, after all.
Now you could criticize Dana for giving Kimbo fights after TUF, but most people find Kimbo fights interesting for the moment, so why not?