When you have lost so many games over such a long period of time you can only do certain things. Nobody LIKES losing but being exposed to it perpetually is sure going to affect how a person responds to it. When you have players that have constantly been exposed to losing, the only thing left to do for them is to re-frame losing in a different way that isn't so damaging to their own ego. That's why you get phrases like "content with losing", it's not that you're content, it's that when you've been exposed to it for so long, you have to re-frame it in a different way in order to function normally. That's why to an outsider from a winning organization it appears ludicrous. Ultimately the vast majority of humans are made so that they conform to the new standard, for the Oilers that standard has become losing.
There are a select few of personalities that push harder and have a harder time accepting losing, but even those need a fighting chance or they'll simply demand a trade or leave through free agency when they feel they can't contribute to a winning team or worse become eventually just as accepting of losing as everyone else. That's why the longer the losing goes on, the harder it is to change the losing tide without removing people who have been in the organization for too long under those circumstances. That's what a "losing culture" means, the people who are in the organization are already operating through those standards and the new people, especially young prospects, are going to be just as infected by the losing culture over time.
The longer it goes on, the more drastic measures have to be made to reverse the losing culture. Things that might have worked 2 or 3 years ago will not suffice now because people from within have conformed to losing so much that a single positive outside influence be it a new player coming in through trade or through the draft, or a coaching change, isn't going to cut it. If an internal evaluation is going on throughout the organization, then the first question to be asked is what moves need to be made to reverse the losing culture and that's where the "real" hard decisions might have to be made, a coaching change is a blip on the radar in the grand scheme of things at least in the context of the Oilers franchise, the grand failure of the "rebuild" regime has been the complete failure on the grounds of instilling structure and a competitive team that plays fundamentally sound hockey even if its temporarily over-matched as it goes through the rebuilding process.