Does anyone else have experience with TeX?  Knuth wrote it in Pascal (I was there when he was considering whether Pascal or C would be the right choice), but most implementations run as C.  Someone wrote a set of support routines plus a translator for the very restricted Pascal that Knuth used.  Local modifications to the code are almost all handled by substituting new Pascal code which is incorporated by a preprocessor before being translated into C.  Really works pretty well, and some of the same techniques should carry over to pypy.
 
I once started a project to translate TeX to Java, but found the translation to Java more difficult than that to C and ended up abandoning it.
 
--Th