1. New, popular system/language/app appears and gradually adds features and complexity in response to user requests as it catches on. Devs are personal and responsive. Users feel engaged.
2. Users grow disenchanted with the increasing complexity of the system. Developers burn out on support workload and slowly become more remote.
3. A new shiny, simple alternative appears and users flock to it with a storm of feature requests. Go to 1.
Of course you want to avoid non-intrinsic complexity, but a lot of things are only simple because they don't really do much.