So I just recently had the pleasure to set up a Rails environment for a friend on Windows. I haven't used Windows in about 5 or 6 years, and the person I had to set it up for doesn't know much about programming at all.

I all went fine at first, install database, devkit thingy and git. Then set up the project itself. And there is where the problems started.

First windows would refuse to use SSL, because of some weird bug in the Windows version of rubygems. The suggested upgrade did not work so I had to switch some gem sources to insecure connections, but at least it did install everything correctly.

Alright, I thought, that's not _that_ bad, everything is running now.

He sent me a screenshot some time later. Something was wrong with the JavaScript runtime, and I could not figure out for the life of me what the issue was.

Later again he sent me another screenshot.
His Antivirus spyware was messing with the asset pipeline. (╯°□°）╯︵ ┻━┻

This was the point where I just said "FUCK IT, i'll just put everything into a fucking VM and let him use that".
I should have done that in the first place.

Long story short:
Setting up a development under Windows is painful.
Do yourself a favor and just use a VM.