I disagree with those who think Bayless can "learn" to be a PG. I did an analysis years ago that showed that the assists/minute ratio of virtually all point guards in the league (excepting Nash) did not substantially rise after their second year with significant play time. I used this to show that Telfair was a failure (sadly, because I wanted him to be awesome).
In other words, over time point guards get smarter, they improve their shots, and they cut down on turnovers. But they do not become better point guards in the NBA just because they were given PT at the position.
Based on this, Bayless may work fine as a combo or 2G, playing with Roy or Rudy. But he'll almost certainly never become a good point guard.
iWatas