I've always thought being a pro sports owner is actually a very tough job to get right, because it is dependent on someone who is a non-expert in a field choosing between different experts as to whose knowledge is superior. And it is in a field where expertise is hotly disputed even among those who are experts. I'm sure that each time Jimmy hired someone, he wanted to hire the best available guy for the job, and thought/hoped that whoever he hired was the best guy for the job. And even though he very likely got some advice/guidance from some "experts", it still was hit and miss. The key for him was the (derided by some even here) move of hiring DePodesta in 2016. DePodesta wasn't a football guy, but he was a sports management guy who could help Jimmy make better decisions about hiring.
I think what we have now is actually what Jimmy wanted all along. He didn't want to be a "meddling" owner. He just wanted the right person at the top so he no longer has to make football-related hiring decisions for which he knew he lacked the expertise. He's handed over the operational keys to Berry, DePodesta, and Stefanski, and no longer has guess about how to haphazardly fix an organization that wasn't succeeding.
He and Dee get to just sit in the owners box and watch, and that's what he really wanted all along.