This may seem like an unusual blog post: why not a post to parrot-dev? Well, I've struggled the past few weeks as a newbie, largely with language syntax. But this problem is different: this is an interesting problem, one that I think shows that language/compiler design is more than just mastering basic language syntax and getting something to run approximately.
For readers unfamiliar with squaak, I think it is a teaching tool, not a finished high-level language (HLL) that would likely be used to get some job done.