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You can save a nice chunk of money if you sign up for a year or more of dedicated hosting at a time. For example, you can rent a GoDaddy dedicated server for $129 per month, but if you commit to a 12-month contract, the price drops to $79.99 per month. Chances are, if you're serious enough about your site that you think it needs a dedicated host, you're probably planning for it to be up for a year. Of course, that's where the money-back guarantees come in, and some sites definitely offer more than others in that regard, so do your research. All our web-hosting reviews cover these guarantees.
The answer to this question largely depends on two factors. Are you new to server technology and not very interested? In this case, Windows is the easiest option to get where you want to go. Do you already have experience with Linux or would you like to familiarize yourself with this operating system? If so, Linux gives you more freedoms to configure your server, and you will be using an operating system that is less vulnerable to attacks from the Internet. Linux is also open source and therefore free.