Ted Dibiase could be a decent shout for MITB next year...
Anyway, how I'd do it: making the Million Dollar Man GM for the night would start it all off, and he'd give Teddy a world title shot because he's his son. Then, in the world title match between him and Orton, Ted has Orton beat, only for Cody to come out and interfere, DQ-ing Ted and Orton retaining. Ted demands a rematch, and his father grants it, but whoever is GM (needs to be a heel) the following week scraps that match, and gives Orton the week off. Instead, he makes a battle royal, with the winner getting a world title shot at the next PPV (I'd do this for Armageddon). Obviously, Ted is entered, and gets down to the last 3, him, HBK and Trips. Trips grabs the mike, and announces something along the lines of 'Dibiase being good enough to beat Orton', and they'd love to watch it at ringside to prevent any interference', that kind of thing. They then both climb over the top rope and give the win to Ted.
At Armageddon, Orton barely retains, and Teddy heads into the Royal Rumble. He goes in early, and does the iron man, staying in until the last 5 or 6 wrestlers, before being chucked out by a big name, like the Undertaker. I'd also have him eliminate a big name heel (Chris Jericho would be perfect) somewhere along the way. At No Way Out, he has a 1-1 match with Cody and beats him comfortably. Orton retains his title in an elimination chamber, and goes on to face, I dunno, HBK in the main event of Mania.
Ted qualifies for the MITB, wins, and cashes it in by challenging Randy to a match at Summerslam. None of this 'cashing it in when Orton's hurt' rubbish, he challenges him to a straight 1-1 match, giving Orton about 3 weeks notice. I'd also make sure that up until this point, the only 2 matches Randy and Ted have is the Raw match, followed by Armageddon. I'd also have Orton acting as a coward, attacking Ted at every opportunity to avoid matches with him.