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Originally Posted by EranB
...Why would I lose any eBooks?, they are all saved in my Amazon account under 'Digital Content'. I will just transfer them to the new Kindle. So there is no loss here.
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Well in your first post when you started this thread you said
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The reason is that I have more ebooks in my device than on my Amazon.com account. Some of the ebooks were sent to my Kindle as a gift and will not show on the Amazon.com's digital media content.
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So you started this thread because you were concerned about losing those gift books and now you're not, but I don't see anything that says how you recovered them or that you did find them in your Amazon account after all. Can you clarify this situation?
In general, if you buy a new Kindle you will be able to download all the books and docs that are in your Amazon account onto it via WiFi.
If you want to use Calibre with the DeDRM plugin installed, then you can download all your books and docs from your Amazon account to your computer and add them to your Calibre library. At that point, the DRM will be removed and you can sideload them onto any other Kindle you may own.
What you cannot do is connect your current Kindle to your computer*, copy the files to your hard drive and then copy them straight to a new Kindle. The files on your current Kindle have DRM that's encoded by the serial number of that device. They won't be readable on your computer or on any other Kindle unless you first remove the DRM. You may be able to do that by importing them into Calibre with the DeDRM plugin, but I haven't tried that myself.
* You also said in the first post that you're unable to access the files on your Kindle when you connect it to your computer. This may be a problem with your cable, or there may be file corruption on the Kindle. Do you see it as a drive in the Windows Disk Management tool?