While the issue of cash flow is not really publically available, the one thing we can definitely say is that the value of the Cubs has increased dramatically since they purchased. So they've definitely "made money" from a value standpoint.
They talked a lot about some of the things like capital improvements being revenue generators though. Whether or not that's generally true or "not yet" true, I think most fans expectations was that the payrolls were kept artificially low in the lean years, but that money would be made available later. It seems like there should be more room if that's the case.
As of Tom Rickett's Press Conference today, they are out of money. His words, not mine.
https://www.nbcsports.com/chicago/c...-machado-theo-epstein-darvish-mlb-free-agency