Owen should have won the strap at Summerslam and held it until the following Mania.
That would've been great.
Owen defeats Bret at WM 10, and then later in the night, stands in the aisle way - stupified that Bret is celebrating in the ring with the faces of the locker room as the NEW World Wrestling Federation Champion. Later in the year, he succeeds Bret as the new KOTR, and becomes the Number 1 contender. At SummerSlam, Jim Neidhart helps Owen win the cage match through some shenanigans and afterwards, he completely ghosts Bret, but brags about being 2-0 against him. The Royal Rumble then comes around and Bret rightfully wins this time and there's nowhere for him to run now. He's facing Bret in a rematch for the WWF Championship in the main event of WrestleMania 11.
You can add some interactions with the Hart family in all of this and have them sitting front row too.
Sorry for the fantasy booking, brehs. This would've been much better than what we got.