You are arguing against yourself now. I think JR is going to operate the same way he has always operated. He isn't going to spend just to spend. He isn't going to suddenly go wild in free agency or payroll. He will probably allow more spending than he has in the past when the team allows for it, but I can say at a level of near certainty that he isn't going to go from pinching pennies for the top free agents on the market to blowing past the luxury cap numbers in the same breath.
If JR was really going to go through some spending spree because he wants to win before he dies, and somehow stop the rationality that has been a trademark of his management of the White Sox, the most obvious place to start would be spending what it takes to get Manny Machado done. Instead he is playing it exactly as he has played it with every single free agent in the teams history, bar one.