DinoDB1975
Super Freak
I'm thinking he will, after all no one in his house respects him. Did you notice the look he had after he mentioned the Starks would come to take whatever place his men were going to take? I think he means to rejoin Robb when that happens. At least I hope.
I took it the other way. I took it that Theon knew that Winterfell would send a large force to re-take the place he was going to raid (I can't remember the name either: I think it was something "Square"), thus leaving Winterfell vulnerable...and ripe for the taking, cementing Theon's worthiness in his men's and his father's eyes.
I like your theory better, though, and I hope it comes true. I like Theon.