Yeah, the story wrote itself after Montreal. Owen came back super hot. Im not sure he could have carried the place as a top guy like Bret but he was certainly super talented and deserved a lot better than the Blue Blazer. He quit WWE after Montreal, not because he really wanted to leave but out of loyalty. I wonder how he in WCW would have worked had he arrived with Bret. But Vince desperately wanted to keep one of the Harts, probably for the Canadian market and to try and repair his image a bit, so they offered a big contract extension to stay which he did.
I'd have considered having him beat Bret for the title in their cage match. Interesting side note, when the brother vs brother angle was pitched to Bret by Patterson, the original idea was for Bruce Hart to be the brother than turned on Bret. Bret said Bruce could never make it work and pushed for Owen. Patterson (and presumably Vince) thought Owen was more a mid card comedy guy (what the hell did they think Bruce would be) but Bret insisted. Bruce was hot at Bret for that.