I think Tony Stark has sufficient intelligence to breach the technological singularity by inventing a computer more powerful than the human brain (even his own) and creating a mind-machine interface capable of uploading his consciousnesses to such a computer. I envision this as leading to the third evolution of Iron Man after the first power suit and the Extremis Armor. Tony would install the supercomputer into a life model decoy of himself, as well as every one of his former Iron-Man suits, and then copy over his consciousness to every one of them, all of which would be networked together and retaining a single identity, thus making him essentially immortal. This should happen in comics now while it's still science fiction, because it all may very well become science fact within our lifetimes.

Isn't that what Pym already did with this guy?

The upcoming Age of Ultron will actually be my first exposure to the character, so I hadn't realized that was the case. Outside of Avengers (vol. 1) #1 & #4 and Ultimates 1 and 2 I'm not really familiar with Pym either.

I think Tony should be less than trusting of his AI capabilities after one of his last big AIs was basically a creepy abusive boy friend. 
Then again he's making an AI based off Pepper Potts so maybe he's just a glutton for punishment...

Yeah, Pym already did that ;)

His AI getting hacked has become a common appearance in his storylines. I think the next evolution will feature him fighting digital interrogations inside his own circuitry Lawnmower-Man style. Or, materials wise, maybe a brightly coloured photon-shield style of armour, rather than metal. Too radical?