The problem we are facing at my company is: we have a federated Jenkins setup where each team got their own instance and my team managing Jenkins updates, etc.
You don't know the pain we suffer from this plugin ecosystem. Installing a bunch of plugins which depends on a bunch of other stuff, there's no real dependency management for this and it's thoroughly painful when one of the teams decide to upgrade one of their plugins and break their whole setup because of it.
It has happened before even with basic plugins like "Git", one upgrade completely broke more than 50% of our instances (we are running about 50 instances right now) because a lot of other plugins relied on it and then needed to be upgraded, these upgrades then broke other plugins which depended on them and this started a domino effect.
Also, some plugins are just released and never taken care of, we have to maintain about 10 forks of plugins because there's no curation about them.
We came to the point where Jenkins flexibility by itself is a liability.
I know that Jenkins is wonderful for smaller teams but there's a point where the lack of governance really hurts and it's the main burden about it.
But of course, that's a given for any flexibility, too much of it and you have to design boundaries to contain problems... I'm just ranting because after this stint I'm burned about Jenkins, to the point where I don't want ever in my life to have to work with or use it.