Now this may be largely a culture thing, with Java programmers creating more cross-platform software and avoiding platform dependent libs just by default, or it may be a technology thing, but to the end user it doesn't really matter.
And this is coming from a linux veteran who wrote a C# web app and hosted it in production on Linux for a few months and then had to re-write it in .NET MVC hosted on IIS. I hate Windows servers. Every time I have to RDP into them to change some configs instead of just vi'ing files in /etc I want to shoot myself.
Ugh, maybe you should try out at least one of the several options for remotely managing IIS before you shoot (or embarrass) yourself?
Not to mention the difference of opinions you get when you search for IIS tuning info/documentation. Half the stuff is only valid for older versions of IIS and there doesn't seem to be a lot of good info on the latest version when it comes to tuning.
http://mono-project.com/What_is_Mono
(hint: search for the word "subset" on that page)
Unfortunately the CLR doesn't run on any useful platforms.