My thinking is this; if I'm willing to fork over dollars to a VPS hosting service for peace-of-mind, then paying for a service that helps me understand what I'm doing when it comes to self-hosting should also be on the table as an alternative.
That said, I have no idea how viable of a business model that would be, or if it would even be able to be developed and upkept with reliable info. Or, maybe it already exists, but on an enterprise level that I cannot afford for some dumb little blogs.