You basically just admitted that Linux boxes are harder to administer than Windows servers. This makes Linux servers much less appealing for companies when you can find Windows server admins for a dime a dozen, but Linux admins are harder to find and generally cost a lot more.
Er, no. Windows makes the easy things easy (pick what you want from the list rather than, horror of horrors, type something) but still hasn't succeeded in making the difficult easy. This lulls people who think they know what they're doing into jumping into the deep end and finding out they can't swim. Lots of things when setting up a server (web or otherwise) that require an understanding of the underlying networking. The Windows admins who don't know this are the ones who are "a dime a dozen." The ones that do can create a secure, functional site with Windows but wish they had Linux since it's easier and more secure and faster and more flexible and....