A question about this:

Shedskin results always #includes pcre.h and -lgc . Does this mean we should 
propagate both or is it expected that the user knows about those or should we 
patch the Shedskin Makefile generator so that it references specific inputs?

If the latter, see shedskin/makefile.py which uses (distutils) 
sysconfig.get_config_var('LIBS') and sysconfig.get_config_var('SYSLIBS') and 
others.

Those are probably Python's compilation flags. Should we extend those or rather 
patch shedskin/makefile.py to also get them from somewhere else?

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