In retrospect Owen in WCW circa 1991 seems like it would have made a lot of sense for both parties.
For Owen- He was barely used by WWF in 1989. His athletic cruiser weight style would have fit better and allowed him to stand out more in WCW.
For WCW- Bret was not a star at this point but was featured a lot on TV and always rumored to be going out on his own and getting an IC title run. That has to be worth something from the perspective of people turning on the TV, seeing Owen and saying "Hey, did you know that is Bret Hart's more athletic brother?"
And lastly, having Owen would have given them a better chance at signing Bret later that summer when they were rumored to be pursuing him, no?
Well, Owen was trying to get out of his contract in 93 before Bret talked him out of it, so it could have easily happened at that point as well. I really think that he should have, just to get the experience of working a different style with a different group of people. He really only got to a certain level as a worker in the WWF and jumping ship might have lit a fire under his ass and helped get him to the World title level. Can you imagine the combinations we could have seen had he been around for 95 Nitro against the Benoit/Eddie/Malenko group?
Plus, you know, he probably would still be alive. So there's that.