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I think you will find plugins need to be reinstalled unless the path for your calibre configuration directory Kovid mentioned above is *exactly* the same on both machines. Because inside one of calibre's configuration files (customize.py) it stores hard-coded full paths to "installed" plugins.
If your directories are different, you can still try Kovids suggestion. From a plugin perspective, at a minimum still copy across the plugins subfolder into your new configuration directory, then reinstall the plugins. The plugins store their configuration data in .json files in that plugins subfolder so it would allow you to keep your existing plugin settings for most of them.
There is the odd exception like the "Generate Cover" plugin which also stores full paths to the images, so you would need to copy those images across and modify the paths inside the plugins/Generate Cover.json file. I should really change that plugin so it stores paths relative to the calibre configuration folder which would make it more "transportable". As a workaround you can use the ability to export your cover settings, install the plugin on your new machine and then import those cover settings.
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