A lot of what you're describing sounds like the innovator's dilemma. One of the things that makes legacy systems so difficult is that everything is there for a

A lot of what you're describing sounds like the innovator's dilemma. One of the things that makes legacy systems so difficult is that everything is there for a reason, but often the reason is to satisfy a small minority of customers. It's easy to look at a component and say, gee this feature is only used by 2% of customers, we should consider dropping it. But that 2% is someone at the company's customer and they will raise hell if you get rid of it. So naturally the system gets filled with all these special cases to handle niche customer use cases none of which can ever be removed. This is when a startup comes along and targets the high value basic use cases and drops most advanced functionality. Then they start acquiring bigger and bigger customers, complexity accretes to meet their needs and then eventually the startup is the legacy company and the cycle repeats. The question as a developer is do I want to work on such a system? For me, the answer is a resounding no. If I agree to work on such a system, I will essentially be enslaved to the bad design decisions made before I joined the company. It will never be truly satisfying to work on that system. I am speaking from experience. But that is why companies pay a salary. The established company mindset is not the startup mindset is not the hobby project mindset. It's up to you to figure out what is best for you at any time and that choice may change as life circumstances change.