First, I really like Bayless. As a player and a person- he's legit.
Second, I don't see him having much of a career in the NBA. I think he'll drift around, maybe find a team to start on a bit...
He's an undersized SG who probably will never learn to be a true PG. He's a true "tweener", and unless he finds the exact situation with a team, he'll just be one of those talented players that doesn't fit into any role.
Nate has stated repeatedly that he wants a PG who can run the team, effectively run various pick & rolls and push the ball effectively (meaning get a defense on it's heels and thereby creating mismatches off the break, as well as penetrating the paint and making the right decision to either go to the hoop or dishing to the open man)- so far, Bayless has shown he can't do any of those.
Does that mean he can't learn? No, he can learn all those skills, but can he learn tham all well enough to lead a team to the very upper echelon of the NBA? Very unlikley.
I hope the best for him, I really do, but I think he'll be an NBA journeyman player.