You're selecting a few of the greatest floor leaders of all-time. No one is saying Bayless is or will have the almost preternatural ability to sense where the ball should go. But those aren't the only players who can be point guards. Using an analogy, the greatest chess masters in the world may have an innate and unusual pattern-matching ability perfectly tuned for chess (which they have to refine with lots and lots of playing). But even people without that can become great chess players, deriving a high-level pattern-matching ability from lots of work and experience.
So, sure, Bayless may never appear to make magical passes, but if he can draw defenders and find open teammates, he can be a very successful point guard for this team. Roy has plenty of play-making ability too, so Bayless doesn't have to be one of the great play-makers in the league. If he can hit shots when playing off the ball and drive-and-dish when he's playing on the ball, he'll be a great complement to Roy.
Remember, Bayless was a point guard in high school and recruited to Arizona as a point guard. He played shooting guard at Arizona due to injury to their planned shooting guard. He has played the role and was expected to at a high level. I think there's good reason that the Blazers have confidence in him to be their point guard of the future.
