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It really depends on what you need. If you are looking to mask your traffic at Starbucks or a hotel there are a number of free options that are fine for occasional surfing/email use. On the other hand if you are looking to mask your location (to get a geographically restricted service, for...

Have you tried ripping an original DVD? If that works, there may be something wonky about the copy you are trying to rip.

Try this for windows: DVD2iPod Guide