You want a smooth progression of tooling that you can approach and slowly clarify ever-finer approaches to over time. The object model is the base of the pyramid, it's the thing you rely on when nothing else solves the problem, you know you can always invent a new kind of object hierarchy by refactoring to BasicObject, obliterating stdlib semantics with a veritable flamethrower. I've never put such a thing into production, because I know there's always less drastic ways to define, mold, shape, and extrude abstractions.
With less semantically-fluid languages, you wind up relying on the same few tricks over and over and over again, because they solve problems, albeit poorly and opaquely. This flows, again, from the underlying approach to typing. Python is dynamically typed, which keeps it from being totally unworkable any time you need to do something special or cross-cutting, which is absolutely a need in the web world, but it's structured enough to where you need to devote library-level amounts of thought into coming up with clean, semantic abstractions that are easily traversed, something Ruby just comes with out of the box.