Agree with the last part. There are some other things relating to the former (which I won't get into here). The only reason I put Bailey ahead of Latos is the fact that we already have Latos under team control for the next 3 (4?) seasons.
I'll reiterate that I would not go more than 3/$27MM with Homer Bailey. He would still be quite tradeable with that contract, barring a major injury.