At the end of his junior season at Indiana, his handle was suspect at shooting guard so it's difficult to imagine him improving it enough to actually run as a point guard. His handle is even worse when he switches to his left hand. Not only that, but he wasn't much of a playmaker for his teammates. As Evan pointed out, Oladipo had 175 assists to 203 turnovers in his three years at Indiana. He really only wanted to dribble with his right hand and his handles are so loose that he was susceptible to having the ball poked out of his possession.
Check out this clip: a left-handed drive that results in a turnover (shouts out to Mike Prada for this and another later video). In this video, Oladipo drives left into traffic and turns it over on a weird bounce pass. Rather than sitting and taking advantage of being face guarded, Indiana forward Christian Watford makes a terrible cut that brings additional traffic to Oladipo. But the concern comes before the turnover. Oladipo isn't able to get past Ohio State's Aaron Craft because his left-handed dribble is too slow, limiting his athletic ability. Craft is one of the best perimeter defenders in college basketball, but with a tight dribble Oladipo should be able to blow by him.
But let's stay positive here. There are some encouraging things about Orlando giving Oladipo run at point. In his junior season, Indiana head coach Tom Crean trusted Oladipo much more as an initiator of the Hoosiers offense. 20 percent of his possessions came off isolations or in pick-and-roll sets, according to DraftExpress. He showed glimpses of promise, particularly in pick-and-roll sets. Check out this pass to Cody Zeller on the side pick-and-roll. He sets the defense up with a left-to-right hesitation crossover. That crossover sends his defender right into Zeller's screen. Zeller's man hedges too hard and Oladipo has the ability to slip a two-handed bounce pass to the rolling big man which leads to an easy bucket on a cut from the baseline.
Oladipo's one of the hardest-working guys I've ever watched and I saw him develop from a dude with complete raw athleticism to the no. 2 pick in the NBA Draft. Mostly every team was impressed with his workouts which suggests to me that he's been tightening his handle over the summer. I really don't think he can play point guard, but there's really no reason that the Magic can't give it a shot during the Summer League.
After all, Summer League doesn't mean much. Yeah, you want to use it to develop your talent, give young guys a chance to play together, and see if any of the lower-tier guys can actually earn a contract, but it isn't the regular season. It isn't even the preseason. In the big scheme of things, Summer League means nothing. So giving Oladipo a shot at running an offense isn't really a big deal. And if it works out, then Orlando struck gold. There's nothing to lose. Why not give the rookie a shot?