I deal with this shape of problem quite a bit. After using scons and make in the past I recently tried using ninja, and it really works well. Specifically, a p

I deal with this shape of problem quite a bit. After using scons and make in the past I recently tried using ninja, and it really works well. Specifically, a python configure script using the ninja_syntax.py module. This seems like it's a bit more complicated, but has a lot of nice attributes. File names with spaces should just work (unlike make). The amount of hidden complexity is very low (unlike make or SCons); all the complexity lives in your configure script. It's driven by a real, non-arcane language (unlike make). Targets are automatically rebuilt when their rules/dependencies change (unlike make). It's more difficult to install than make, but only marginally.