My take for what it's worth has always been a kind of both/and situation. Yes, I think management are largely lackeys that Nutting has in place and Nutting is the root cause of the problems in the Pirates organization. I don't think any other owner would be just as bad, simply because it depends on who the hypothetically different owner would be. The Orioles were largely the same way and it seems like the new owner will be better, though we'll see how it actually plays out.
But other teams either spend reasonably at least sometimes (Brewers), or they have been able to do a lot better at sustaining success while not spending much at all (Rays, Orioles, etc). The Tigers are generally a big market team who can and will spend a lot, but they have been in teardown and rebuild mode multiple times and might be making the postseason this year.
Cherington's leadership has brought about some good results, as I don't think we can just ignore the state of the pitching throughout the organization. At the same time, I think at least some of that is due to lucking into Skenes. Without him, we'd probably still rightly have some optimism about Chandler or Harrington or Burrow etc., but the whole thing would look a lot more bleak.
I think bleak is a good word for the whole situation. BDLC stinks. IKF is alright, but not much of an answer at shortstop. The rotation might be very good, especially if Chandler shines early and Jones solidifies himself. The bullpen probably stinks, but bullpens can be fickle year in and year out. We won't sign any meaningful free agents or make any big trades. Short of Termarr having a Jackson Chourio/Merrill type rookie year, there's no impact internal talent on the way. Maybe the only slight silver lining from the latter part of the year is that Cruz has taken pretty well to the abrupt move to CF and also cemented himself as a real offensive force.
But the prospects are basically for this team to be the same razor-wire mediocre group that can go on good runs sustained by incredible pitcher, all the while hoping that the really favorable landscape of the division and NL (and really AL) is still there next year. It feels silly to even be saying stuff like this now, but if we had actually made a run after the ASB instead of collapsing, we'd be thinking that we have a true shot at winning the whole thing. There are no real juggernauts in this year's group of teams -- IMO, the closest is Philly, and we won the series with them this year.
The tldr; for me is that I think the situation and opportunity outside the team will change next year, but the situation and MO within the team/org will not change much. Blah.