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I learned it the hard way with Wordpress. Lost much of my stuff. It's a lot easier now depending on which host you use. Some provide a one button upgrade. No matter what way you go, make sure you back it up completely. The worst that can happen is that you just reupload everything and tweak whatever little things may have not worked perfectly. You will also have to upgrade all your plugins so that they can work with the higher version of WP.
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