This isn't some TV drama, and this isn't the same era as the Roy/Eisner fight with Save Disney. The company is in a much better place than back then. Its on solid financial footing, something that couldn't be said in the later Eisner years.
And I don't think its some hidden secret that Iger is using this time until his official retirement date as a way to have a long transition period. I've even said as much in many other posts. This is basically an on the job transition where Chapek over sees the day-to-day. And then Iger does what he does with the board and whatever creative project he wants to work on, while still being there for questions or to step in if needed to take over if Chapek fails.
Iger's compensation package was a small base salary and then all stock incentives based on company performance, his retirement package is pretty much the same, small severance with an all stock award tied to company performance with x amount of time before he can sell any stock. Basically a standard CEO retirement package, to prevent just taking the money and running. This is why its not as you state, that he jumped ship for his retirement package. Because any "golden parachute" that you think he has basically just became a "bronze paper weight" when the stock took a hit due to COVID-19. All his money is pretty much tied up in Disney stock. So he has a financial incentive to make sure the company stays flying as high as possible. After all he is still one of Disney's largest single stock holder. So again this idea that you have that he just cut and ran when COVID-19 hit because he got some big payout is a false narrative.
Its amazing what you can learn if you read the 8K filings.
And then its the same with Chapek, small base salary and then all stock incentive based on company performance.
As for Rasulo and Staggs, as I understand it the board didn't like either of them for the CEO job. Probably many reasons for that, but overall if the board doesn't approve the candidates, Iger can't just appoint them anyways. So no matter what it wasn't like the job was Rasulo or Staggs for the taking and Iger just ripped it away from them because he decided to stay. He stayed because the board didn't have confidence in either of the two candidates the public thought were the front runners.
I doubt an insider would be brought in at this point, just a feeling. There are still plenty of candidates inside the company they can be tapped first before having to go outside. Plus they could have gone outsider anytime in the last couple years if that is really what they wanted. So no I think they stick with an inside candidate.