IMO, the more complex a system is, the more fragile it tends to become. The same is true for programming languages. Features will clash with each other. You'll end up having 10 different ways to achieve the same thing, and it won't be obvious which direction to go.
Furthermore, I did my grad studies in compilers. I've thought about writing an optimizing JIT for Python. I really feel like CPython is needlessly slow, and it's kind of embarassing, in an age where single-core performance is reaching a plateau, to waste so many CPU cycles interpreting a language. We have the technology to do much better. However, the fact that Python is a fast moving target makes it very difficult to catch up. If Python were a smaller, more stable language, this wouldn't be so difficult.