On May 29, 2016, at 6:30 PM, Jason Pyeron <jpye...@pdinc.us> wrote:
> 
> I feel I am making things way too complicated.

Yes. :)

> I have a Makefile, which is building a static library [1] in both 32 and 64
> bit.

Don’t do that.  The 32-bit and 64-bit Cygwins are fundamentally incompatible:

  http://stackoverflow.com/a/18333049

If you must do 32- and 64-bit Cygwin development on a single machine, it’s best 
to have separate 32- and 64-bit Cygwin installations which do not share any 
files.

I’ll add one exception to that, which is that it is fine to share a tree for 
building packages with cygport between two Cygwins since it knows how to 
segregate the build products for you.  It is possible to do this by hand, too, 
but it’s enough of a hassle that you could easily skip a step and end up 
commingling binaries of different word size, causing yourself problems.
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