I use Homebrew and CMake as well, but it certainly has not been as smooth as my CMake scripts contain a series of fixes for MacOS. I also like CPack, but there

I use Homebrew and CMake as well, but it certainly has not been as smooth as my CMake scripts contain a series of fixes for MacOS. I also like CPack, but there's been less consistency with MacOS. Bundles don't work for multilanguage libraries since things like mex files can't be packaged as a framework. PackageMaker was deprecated since Yosemite. OSXX11 is really X11 specific. DragNDrop sort of works, but it can't run any post install scripts to do things like set environment variables, which, again, the process for doing so changes from release to release and whether or not we're on the console. Conversely, the WIX generator on Windows allows me to package everything as I need it to. Though less nice, NSIS also works well. Certainly, that's not to say that everything is rosy and cherry on Windows. I just did a cold build from scratch on a new Windows license and it honestly went as well as it did because I know exactly which tools to get. Mostly, it's that after banging my head against both the Windows and MacOS ecosystems, I can build a new development system vastly faster on Windows and have few headaches. As a quick note, thank god for the Homebrew crew as that does make things much nicer. As a final note, some of these headaches would immediately disappear if I could virtualize MacOS since it would fix the console login vs desktop login problems. Also, I could actually fix problems when working on an airplane.