Been running Windows for a while now. If you keep up with the updates, pretty hard not to do since by default it will download them for you when they are available, it will be secure.
I was a Linux zealot, lived by the command line until I put my first Windows server online. Now I would never go back. It takes me 15 minutes to upgrade mysql or php when new versions are released. 10 minutes to add a new domain to DNS, 10 minutes to add a new virtual website. Everything is point and click. Duplicating a websites configuration to move to another server is easy. There is nothing that can't be done quickly and easily.
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