I don't think it is the smartest choice, but considering we have already sunk assets to compete soon, then yes I do think acquiring a superstar would be the best choice for the given path Chuck has chosen. Let's not act like its Chuck's master plan to slowly build the team up, he clearly simply struck out on Gaudreau.
Teams can "demand" whatever they please. A good GM negotiates that price down, and uses my sales pitch like I gave in the previous post (Only 1 year left, flippable at the deadline, virtually a free 1st round pick, etc.) Given Chuck's track record of paying absolute premium prices in deals, it is not surprising that his negotiation skills are lacking.
But again, it was not even JVR's contract that was the issue. JVR's contract was the one being discussed because it is actually the most reasonably likely to be moved. There is zero chance anyone is going to take on Risto or Hayes' contracts, both signed by Fletcher, which are far more burdensome.