Now I agree with you there that from Vince's point of view, he must prepare for the worst and with WCW snatching up WWF stars at the time, Vince was definitely paranoid. With that said, as Bruce Prichard, Pat Patterson, Slaughter and JR mentioned, Vince knew by May of '97 that he wanted out of the contract he signed with Bret. In June, Vince first approached Bret about the company's hardships. It was September when Vince approached Bret about deferring money from Bret's contract and putting it on the back end. So even all of Vince's henchmen said this could've been avoided if Vince took the title off of Bret at Ground Zero or Badd Blood before Bret officially signed with WCW yet Vince let Bret continue as champion into the last 30 days of his contract, where both parties fell into the reasonable creative control clause. Better yet, why even let Bret be the champion in August when you knew you were going to try and cut him loose?
It was a mess all around but as noted before, Vince held all of the cards as he should as the promoter but then he gave the power to Bret since Bret let him out of the 20 year contract. Vince should have jobbed Bret in September, or October or has Bret lose to a streaking Austin, or back to 'Taker who Bret won the title from at SS. Taker could've passed the belt to Shawn at the December DX IYH PPV and then nothing would have changed going into RR'98 with Shawn as Champ and 'Taker as challenger. Better yet, not put the title on Bret at all.
The only reasons I can't say it's Hart's fault is because he had reasonable creative control, Shawn was a dick, and he was willing to lose to anyone but Shawn (since Shawn had clearly said he wouldn't lose to Bret).
Terry Funk's take on the situation, in my opinion, was as unbiased as you will ever find and Terry Funk is one of the rare gems in wrestling where no one EVER has a bad thing to say about Funk.
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