The money/market thing just becomes an excuse after awhile. They paid to keep Reynolds, Hayes and Keller, and look what they're getting from those guys this season.
Their are other small to mid-market teams who lose players, but still manage to be competitive much more frequently than the Pirates.
It's just a terribly run organization that cannot scout, develop or coach for ****, and this has generally been true through various front offices and coaching staffs over the past three decades.
It starts at the very top, as ownership has been the one constant.
How many talented players never fully realized their potential until after they left the Pirates? Jason Schmidt, Aramis Ramirez, Jose Bautista, Gerrit Cole, Tyler Glasnow and Joe Musgrave are all names that come to mind in that regard.
Unfortunately, "cheapness" is just one short coming of the Bob Nutting-owned Pirates, as even if he became willing to spend more money, there's little evidence he would know how to spend it effectively.