As for "CLI installer" (I presume you mean the installer for the CLI git client), and Cygwin, I'm not sure what to say. I've used the Git installer dozens of times without problem, there aren't exactly tons of places for it to go wrong. Are there specific or particular issues you have with it?
I do indeed forget that some programmers manage to make it far resisting learning to use the command line. Even with step-by-step instructions. I guess at some people I'm willing to fault the developer rather than tools that are powerful that come with good documentation.