That frustration is why I like to say that design is language specific - unless you want to do a ton of work to take a language capability and port it. Multi-language VM's are a pretty hard thing, too - the VM's that exist were very much designed with their main language in mind - Java on the JVM, C# on the CLR. Sure, there's a port of Python to both - and in the case of the CLR, it sounds like the author is, for all intents and purposes, creating a new VM on top of the CLR - i.e., treating it as another hardware platform.
We looked seriously at using the CLR as a place to run Cincom Smalltalk, but found that it was utterly unsuitable - we would have had to treat the CLR as a new platform, and write a new VM on top of it. The CLR simply doesn't have suitable support for a language like Smalltalk. Don't even ask about the JVM - it's been frozen for years, and any Smalltalk running on it is going to be slow. Really slow.
Neither Microsoft nor Sun are acting truly motivated to support dynamic languages - at least, not if you look at what they actually do.