It seems like people have this conception that every team takes in the same amount of revenue, and it's just the evil small market owners that refuse to put in their own money unlike the benevolent big-market billionaires.
That's not how it works.
There is fundamental structural inequity in baseball. If you're a big market and you make a ton of money - guess what, your GM has more money to spend!
So the direct response to when our ownership will "pony the hell up" is: never.
But it seems to me this sort of argument is disingenuous, or at least tautological: What lineup is able to win 4 playoff series - well the one that won 4 playoff series, of course.
That is ONE team each year. Are all the other playoff teams fatally flawed? Or just maybe is that how playoffs work? If the Dodgers fail to get to the WS, is that a fundamental flaw in their lineup (I mean, they're seriously lacking in pitching, so maybe)? Or just October randomness?
But it's no fun to ascribe to randomness when you can instead hold someone accountable for.