I've seen instances where improvements and updates are made to existing systems that works just fine. The reason being optimization of resources like time, manpower and money.
But these improvements create new problems in the system that requires another iteration of improvements and updates.
It either that or the intuitive nature of the system is compromised. This creates a very unpleasant experiences that makes no sense.
Another important reason that comes to mind is unrealistic expectations from the IT industry. I've seen customers asking for features that adds no benefit to their business and they want it just because it's out there and they want in. Customers these days want everything. They want an amazing UI, light speed data transmission, quantum level security, and a sophisticated technology stack. They want all this in 1 month. The IT industry is so dense in countries like India that even though these people know this isn't possible, they still promise a product to the customer for fear of losing a valuable business venture.
This inturn results in a half cooked product that seems to have everything the customer requested but whose stability and usability isn't vouched for. More and more updates are promised to solve the issues with the product since "this is an iterative evolving solution".