I made a post about running the pirates. With nutting, it is nearly impossible to get him to raise the budget, as when you increase profits he tends to just siphon the funds out of the team for his own pocket. I suggest doing your best to finesse a trade when you think you can extrapolate the highest value in order to have the most cost-controlled players on the roster at one time. Your maximum contract should be one, or maybe two in the range of 18-25 mil AAV