The problem with near market monopolization, oligopoly, even the singularity, the fail-case is catastrophic and may even wipe out decentralized, diffused, dispersed, decoupled system solutions that can't make it due to so much relative size from the big fish that it squashes them along the way. The bigger the ship the longer it takes to turn.
This Cloudflare issue is like the recent Facebook SDK startup crashes where everyone has a single point of failure on Facebook SDK where people should be using or able to use the OpenGraph API directly as they need which is more robust to the app that uses it, it won't crash on startup.
In business it is a goal to centralize to grow, in nature and robust systems it is more differentiation and decentralization to survive. There will always be a push and pull between these two forces.
Systems and markets are like gardens. The garden must be maintained, new seeds planted and helped to grow from small to mid-sized, mid-sized plants the bulk of the garden, and then the larger plants need to be culled back when they get too big to not take the mid-sized and then all the resources from the new seeds/small plants. The problem is we have allowed the top end to take over the garden and when they fail they fail spectacularly. The bigger the scale the bigger they can fail.