I don't understand the point here. Jackson got released by the Eagles and signed to a good contract by the Redskins. Vets who have bigger contracts than their contribution warrants are often released by their teams. It's not like NFL vets have ever had any security. Expecting that to change is unrealistic. Again, what would you have the players do? Should they take the hit so that future generations of players have a more secure hand? Should these players give up a year of their 3 so that future players will maybe have 5 year careers? What's the benefit for the current players?
The bold is the difficulty in all of this. If you have a great QB that's older, you are probably paying them like a great QB. If you are paying them like a great QB, it will be more difficult to field a good team because of less money and worse draft picks. So you need a young QB playing good enough and with the rookie wage scale, that's even cheaper than before. With that young QB playing good, you need high paid players elsewhere to play at a high level and so on to win the SB or even field a consistent playoff team. The other side of that coin is Peyton Manning and Drew Brees who you mentioned. They were great QBs on a large contract who won a SB. (Eli might fall into this category but well the Giants are always an exception). The problem when paying the big money is that you use the great QB to cover up weaknesses where you cannot spend money. That could be offensive line, running backs, wide receivers, tight ends, or many positions on defense. You have to rely on less money. The problem is if the QB is covering up a weakness is that it leaves your team vulnerable when you play great teams consistently, like you do in the playoffs. End of the day, it seems the trend is win when the QB is young and maximize your chances in that small window, and after that good luck. The Ravens were oh so close, in my opinion, of getting Flacco at a reasonable contract. Then Flacco had the best 4 game stretch of his career which also coincided with the Ravens playing some great team football and little bit of luck. It created the unique situation where salary cap wise, winning the SB was worst outcome for the Ravens.
Seattle doesn't need to win another SB to give Wilson a big guaranteed contract. He hasn't even hit his prime yet and already got the job done albeit with a stacked team, what more does that franchise need to know? Flacco is literally 1/2 the QB and 4 years older and Baltimore crippled themselves forever just because he won one. The SB winning QB always gets overpaid, just look at Eli and Flacco there are plenty of other examples but nothing more needs to be said. Wilson makes those two look like bums, he's getting paid. Teams get held hostage because you can't blow up the ready made win-now roster to start fresh on a QB draft pick bargain hunt. So they're forced to get rid of a couple other big contracts immediately or put themselves in cap hell a few years down the road to keep the core identity of the team in place when the QB contract comes up. Seattle happened to hit a few superstars on throwaway draft picks so they'd probably prefer to extend a 2-3 year loaded roster window and suffer the consequences for a year or two after that to try getting another ring or two. Then if Wilson blossoms into the next Manning or Brady after cap hell you might get another shot or three in his 30's. That's the idea anyway. Plus the financial pressures to retain the SB winning QB strongly compound when you factor in the 9 figures having that player around will add to the team in merchandise sales, branding the team, etc. Good QBs put good teams over the top, and when they do those are among the main reasons why the team gets held hostage by them and that won't change. Kap is unique because he isn't that good (at least yet though he likely never will be) and the team got to look at the mountain but didn't quite get over the top. That situation is pretty rare, I'm having a hard time thinking of anything approaching comparable in the past 20 years, so that's a much likelier explanation than any greater understanding of team dynamics driving new trends in asset allocation. I mean you could argue that if the players got united behind the cause of raising the cap to a fair percentage of the profit the players generate and to change the CBA rules to extend the average career shelf life from 3 to 5 years a strike could be worth it. You lose a year striking but gain two years in shelf life that's a year netted. The problem is guys that only have one year left due to age and wear and tear still get screwed and the owners would literally riot. I imagine it would be more profitable for them to sit out two or three seasons rather than start paying out their fair shares in salary ad infinitum. So the threat is you're automatically going to ruin the tail end of 5-10% of careers if you go to war and if it gets drawn out you're going to ruin a lot more than that which will cause the players to cave when an inflection point gets reached. The other side of the coin is owners reach their profit inflection point first and you win. But with salaries making everybody a comfortable net worth and some very rich, players are unlikely to find the balls to fight to stop getting robbed blind by the owners.
The real problem is that at any given point in time the average NFL player only has a couple of years left in his career. That's true for the 23 year olds who will be out of the league on talent and cost issues by 26. It's true for the 27 year old vets who will be out for similar reasons or playing for vet minimum at best by 30. It's true for the 32 year old vets who are by some miracle still playing and getting paid. An NFL career is a "grab-it-right-now-because-it's going-to-be-over-in-a-flash" proposition for 90% of the players. Getting them to sit out a season, which is the only credible threat that a striking sports union has, is like herding angry scared cats.