I'm not sure that it matters as much anymore. I used to work for an
all Windows shop that did ColdFusion and Adobe CS3. So I approached
Ruby from Windows. I found that it was fine. Now, I code in Mac OS
X, which is also pretty easy to do.
I have a slight preference for Mac or Linux because I prefer to use a
terminal sometimes. Its nice to be able to open terminal and type irb
and try an idea.
In either case, I think the more critical choice is what sort of IDE
you want to use. I use NetBeans and that works really well for me.
I used ruby on both OS. I just felt that i got better performance on
the MAC.
I don't have workbenches or so. just when I rum my unit tests. The
MAC was much faster....
It seems that people are making Rails development happen on all 3 major
platforms (OS X, Windows, Linux), so in the end it comes down to what
you prefer, and are comfortable with. That being said, I would
personally recommend Mac OS X or Linux over Windows. Working with rails
(or really any web programming) without a terminal by my side would be
frustrating for me. I think once people are comfortable with the Unix
command line, they realize it has major advantages over anything Windows
has.
I would also argue that software like Ruby, Rails, Subversion, mySQL,
etc were originally intended to run under a Unix environment, and that
much of the documentation on these tools assumes you are, too. Also, on
OS X, you can use Textmate, which is a great editor (although to be
fair, there are tons of great cross-platform editors - I use jEdit when
I'm on Windows).
I really can't make a direct comparison to Windows. I had a bad
experience in the earlier days of Rails trying to get it running through
Apache and SCGI, but I would hope that Mongrel makes it much easier now.