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A DRM-free ebook is DRM-free forever. So if you stripped DRM on import to Calibre, those ebooks are still DRM-free. You can check this by viewing them in Calibre (a DRM-ridden ebook won't open for reading).
You may need to re-install the DRM-stripping plugins for new purchases, depending on how you copied over Calibre. You will also need to install desktop ADE and authorize it to your old AdobeID.
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