Why do you want to develop ruby (or anything else) with windows? Especially since most servers (where ruby is popular) are linux servers? All colleagues I've had running windows always seem to have to jump so many hoops that the *nix crows don't.
Also, no unix shell and package managers, how do you deal with it?
It is only Ruby which is difficult to keep up to date on Windows. My question was to try and find a solution.
I have tried using a VM (VirtualBox and VMWare), but it is not a desirable work flow. I currently use RubyInstaller.
There's shells for windows very similar to (some of which are ports of) unix shells, and chocolatey exists.
But it is still my preferred language for scripting and automation on Windows.
Is the issue of using ssh/CLI the issue? If you plan to use Ruby professionally, you're gonna need those skills.
Additionally, some things like Redis, common to many Ruby apps, just won't run on Windows.
My question was more of a concern for the future of my current dev setup. I was hoping someone on HN would know of a better solution to install Ruby on Windows manually, without having to wait on RubyInstaller.
I will check out Vagrant as you suggested.
Yes, you can build from source.
OTOH, unless you want to develop windows-specific Ruby software (or work specifically on improving Ruby-on-windows), you are probably better off using a VM -- vagrant is your friend.
(if possible, it's usually ~24 hours until the windows packages come in)