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The problem with a windows server for adult sites is that your going to have to buy more software to do what you want. If you want to start a membership site, you need to buy some software to password protect the areas properly. Most software for Windows will cost you. Most software for Linux will more in likely be free or cheap. There is also more software out there to run a paysite on Linux compared to Windows.
Bottom line is that it will cost you money everytime you want to add software on that Windows box. On a linux it will be free or cheap.
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