I’m using a plugin called TurboCSV (found here, at the time of writing). The plugin offers support to add data to your various custom fields, which need to be created before the import takes place. In my personal use, I was able to successfully import thousands of items from one .csv, including hundreds of taxonomy terms and custom fields.
Have a look at the plugin’s documentation to see how involved it is and how much you’re able to do.
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