I've finished packing dozens of Catalyst plugins and now http://ppm.tcool.org has about 140 Catalyst plugins (including models/views/helpers), that is, more than half of them at CPAN, though some of the most important modules are missing, including the ones which call for Cache::FastMmap.
So, I agree developing some kind of Cat apps (especially smaller ones) on Windows is not so hard as some of you might think, and I also agree, if you're going to create larger web services, developing on Windows is quite hard, or sometimes simply pointless. The best choice depends on what you want to do, and what you're given.