Yeah I'm not saying Middleton is a bad owner by any means. A vast improvement over not just Giles financially but also Monty temperamentally. But at the same time, he was part of the both of those eras [or his father was], and if the bar is now the Dodgers and Mets and various other hedge-fund/private equity ownerships, getting to $301 million and then apparently being unwilling or unready to spend or absorb another $20 or 30 million seems curious, and perhaps even a bit of the old Phillies gentility compared to the brash Mets owner and financial disruptors of the Dodgers ownership. The recent expansion of the ownership group even suggests a return to more of the Giles model, even if Middleton still has the hammer.
But mostly, it took him a few years to get it right. The way I see it 2016-2020 may as well have not happened, other than on the major league roster. He was not yet a good owner and he hired a terrible PBO who hired a flawed GM, and that trickled down to the manager and the scouts and development guys too. And you can argue Barber [hired by the Klentak/Middleton/Girardi] hasn't been a home run either, just that he cleared the very low bar of the two guys before him.
So unlike VFK I don't find the lack of progress especially surprising, and it's not like there haven't been any positives whatsoever.
Of course, "how long should we give him?" is a rhetorical question since he's the one guy we can't fire.