@kevinlozandier… I know what you mean - it’s amazingly broken! I originally started trying to develop Rails on Windows, switched to using cygwin (got that somewhat operational) and finally threw in the towel and moved to a native Linux machine. That has it’s own problems, I assure you, but overall it’s a WAY better alternative.
Have you tried Vagrant for getting a virtual linux machine up and running on your Windows box? If I didn’t have another machine available, that’s what I would do.
I’ve used Vagrant before (and recently tried out Docker), but I’ve since solved the problem to have somewhat of a passable experience with VIM on Windows.
I feel nerfed not having Tmux available to me honest; I’m using pathogen on Windows, but I use Vundle on Mac & Ubuntu.