In my opinion the reason Jerry can't win is not based on his contract negotiation skills. It's because he needs the credit for winning and won't let his coach have the authority and respect of the team. Mike McCarthy instead of Urban Meyer type of crap. Jason Garrett instead of Harbaugh.
Jerry got out ahead of the Jaylon contract. Maybe too far ahead but its not just Jerry evaluating these players.
The reality is our cap situation is not why we are or will not win.
I agree with your points. I would add that his negotiation skills and how that is impacting the cap will be on the long list of why we are not winning.
I guess what I'm depressed about is Jerry and his son are establishing a pattern of caving to the player's demands and not holding their ground. They did it with Zeke, Cooper, Dlaw, etc. and now they have done it with Dak. The weakness of the front office is depressing and it goes along with the issues of wanting all the glory, not hiring a coach, demanding to be the face of the franchise. Now with all those ongoing problems with the organization's leadership we get to add poor contract maneuvering and caving to players.
Bill Belicheck and and Robert Kraft let Tom Brady walk. They made the hard, and very unpopular, decision to let Brady go and blow up the team. They allowed themselves to suck for a year and purge their roster of bad contracts. They did not bow to the GOAT's wishes. Brady left and won a super bowl.
Keep an eye on this situation. Belicheck and Kraft let the player go a year too early instead of 3 years too late. They let their 6 time super bowl winning QB leave the building because they didn't think he was worth keeping and they kept their personal feelings aside. The Patriots are a well run organization that will make the hard decisions on players and not enable them. The Patriots will win a playoff game before the Cowboys will.
But I completely agree with what you're saying. I'm just adding we have 2 or 3 more things to add to the long list of why our organization is so dysfunctional.