I actually agree with much of this, but I will say Jerry has negotiated hard before. Going back to the great 1990's teams, Emmitt Smith actually missed 2 games one season (1993) because Jerry wouldn't make the commitment Emmit wanted. And more recently D-Lawrence played a season under the franchise tag because a deal couldn't get done with Jerry.
To be clear, I'm not putting all the blame on Jerry for these things. Jerry has to look at all things, including what he feels is manageable for the Cowboys. But it does show Jerry doesn't always simply cave in and pay whatever a player wants.
....Im not defending Jerry and think a lot of this is due to the poor contracts he's given over the last couple of years.
Like yourself I agree that there isnt one side at fault and there's a trace of bad luck which goes back to:
1) The draft (the extra year of control and additional money if he had been drafted higher).
2) Replacing a popular hero, whom some wont let go of.
3) Having a statistical down year (QBR) in 2018, the year where he's eligible to negotiate his contract.
4) The CBA to come into effect by 2024.
5) Being on a team that's last in CAP availability for the next 4 years.
6) A new HC who starts a job and not have any money to spend... MM MAY want to spy before he buys, after all if we sign Dak to big money we've got very little left to patch team weaknesses.
7) A HC who has made a tough decision and played Rodgers over Favre.....he could want his man.
What i'm saying, not to yourself in particular, there's more factors than just we should have paid him and i hope with the offense he's got Dak is a major force, gets us deep into the playoffs and we are all aboard about paying him.