I am currently developing a C project under Linux and Win32. The \'deliverable\' is a shared library, and all the development is done under Linux with the GNU tool chain. I am u
As a primary advice, I suggest using libtool, autoconf and automake; they make cross-compilation very easy, and much easier than CMake.
If you are going the hand-crafted route, I would suggest going with different targets. Switching between makefiles tends to hide otherwise obvious errors in Makefiles, e.g. duplicately used objects with different rules. Example: The object foo.o is compiled for the DLL target and for the .so target, but with different flags. If someone switches Makefiles, the existing .o file with wrong flags is used, breaking the build. If you are using one Makefile, this will become obvious through rule conflicts.