I just don't think it's possible for a small market team to make it in this day and age. We are essentially a farm club for the big market clubs and I don't see that changing until Athletes share the same salaries we all do
Professional sports are quite different than the more conventional jobs in society, as the athletes themselves are the product.
Noone is paying to watch someone build a house or car, rather they're paying for the house or car itself.
Plus, it's a supply and demand thing in that only so many people can do what professional athletes do at the level they can do it.
As for the Pirates and the perceived small market barrier, it has not stopped other organizations with similar money as the Pirates from being competitive much for consistently.
It's not to say economic imbalances do not exist in baseball, but the Pirates are just an incompetent organization, and it starts at the very top.
Within whatever limited capacity Bob Nutting might actually care about winning, he clearly has no idea how to go about it.
He's hired numerous front offices and managerial staffs at this point with more or less the same results.
Ben Cherington and Derek Shelton have had their chance, as five years is ample time to prove your worth and the Pirates have gotten no better during that time.
In hindsight, the Pirates would have been better off sticking with Neil Huntington and Clint Hurdle. Despite the struggles they were having, they at least demonstrated they could win over a few year period.
Ultimately, nothing will change until ownership changes, but the Pirates somehow remain too profitable for Nutting to ever want to do that.