I'd argue that there are some major concerns with the makefiles if they require the use of 3 different versions of make to get it all working - a situation I've never personally seen before. I'd suggest prioritizing fixing that before attempting tracking down the cause of other issues. As it stands, there are too many points of interaction to attribute any bugs to any one program.
That said, Windows has never been a strong platform on which to run make (or git, gcc, or any other [u/li]nix originated CLI tools). When I hear of folks using make, I tend to make the assumption that they're running on a [u/li]nix or BSD derivative.
I've already had one upstream patch rejected on account of the additional complexity fixing it introduces, and would rather not indefinitely support my own fork of other people's build setups.
Or if I am going to indefinitely support my own fork, I might as well rewrite the build config to properly integrate with the rest of whatever build system I happen to be using - at least then I'll get unified build/compilation options etc.
That said, Windows has never been a strong platform on which to run make (or git, gcc, or any other [u/li]nix originated CLI tools). When I hear of folks using make, I tend to make the assumption that they're running on a [u/li]nix or BSD derivative.