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You will have to register the Kindle via wi-fi at the beginning, or you will not be able to create collections, or download books for it.
There is no reason not to trust Amazon's cloud. Hundreds, if not thousands of large businesses use Amazon's cloud services, with no problems at all. Why would their own use of it be any different?
Also, you are going to be using the cloud, whether you want to or not, as all your books will be stored there, for future download. And, you realize, that if you back your books up to the pc, that if you get a different Kindle in future, that you will not be able to use the backup copies on it? DRM prevents it.
It would be much more convenient for you to just get a wi-fi router, and install it. They're very easy to install. Then, you could easily download books via wi-fi.
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