I dunno, your jet fighter analogy seems to be working against you. The U.S. Navy's front line jet fighter of the 1970s was the F-14, and the last were retired from the U.S. Navy in 2006. Supposedly Iran still has some operational, left over from the Shah's air force, a few kept running by cannabilising others for parts, but that's because nobody will sell them newer fighters. The F-14 was not in any way a failure, it's just that technology improves.
Yes, I agree on some levels of course, but there's a difference between "technology" and "platforms/airframes." The F-14 was retired for various political and budgetary reasons, not because it wasn't a platform that could be upgraded.
Look at the new F-15EX, for example.
The F-15 and the F-14 were pretty much contemporaries of each other. In fact, both were demonstrated to Iran at the time, and Iran chose to purchase the Tomcat. But the F-15 airframe is still completely relevant almost 50 years later because they've upgraded the engines, avionics, sensors, etc. In fact, there are many arguments that the F-15EX is as relevant as any 5th Gen fighter in the sky due to it's role and the upgrades that have been made. The Tomcat could have remained similarly relevant.
Even in-universe, it makes no sense. The
Excelsior-class spaceframe was still relevant almost 100 years after it went into service as was the
Oberth-class and the
Miranda-class. So, obviously Starfleet was starting to develop designs that would be upgradable and have multiple decades of life, or more.
I'm even of the mindset that the refit
Constitution-class starships were retired too early. At the time the
Enterprise was refit, it represented a major overhaul in tech, engine design, and capabilities. And Yet by TUC, maybe a decade later, they are retiring the class and you never see one again.
Heck, even the casual throwaway line played for laughs in S3 Picard about the destruction of the
Enterprise-E was handled pretty poorly (and I loved S3). The
Sovereign-class was a frontline starship.
But, we know the real "why." For whatever reason, the producers want to stay away from the "familiar" shapes of the past hero ships. Combine this with the fact that they all want to be credited with designing yet another Enterprise, and you have situations in-universe that make no sense unfortunately.