In this specific case, I side with the stated opinion of one of the most admired businessmen of all time, Steve Jobs. Bill Gates just has no taste.
After reading this description of the Courier, I don't know why even bothering Gates with this.
edit: another explanation could be blame shifting. Ballmer knows his tenure has not been exactly brilliant and canceling a project that could be (it would be portrayed as that, if convenient) the iPad killer Microsoft's board dreams about would end up being ammunition against Ballmer in any future conflict. By delegating this decision to Gates, Ballmer is safe. Killing the Courier was the right thing, but Ballmer needed bigger balls than his own to kill it.