You might enjoy reading http://www.tedunangst.com/flak/post/technical-debt-and-tacki.... To address your points:
> Fun fact: Wasabi has more unit tests than FogBugz.
> It’s fully debuggable in Visual Studio. Breakpoints, variable inspection, single stepping, the whole enchilada.
But the whole post makes it clear that working in Wasabi wasn't nearly as difficult as you think.
I won't categorically reject the idea, for instance I think Facebook writing their HipHop compiler was completely defensible. But you need people with compiler experience, and people who know the pain of working with crappy, undocumented, buggy toolchains to make that decision, not people who once took a compiler course.