Failed to import Media

I had a very similar problem when I moved a WordPress Blog from a single WordPress installation to a Multisite installation with different domain names but same IP.
I found out that the problem is the wp_http_validate_url function which drops the URL if the source IP is the same as the destination IP.
You can add a filter wp_http_validate_url to prevent this and allow matching source and destination IPs:

add_filter( 'http_request_host_is_external', '__return_true' );

Please see this answer for detailed explanation of the filter hook and why you should remove it after the import: https://wordpress.stackexchange.com/a/123313/75573

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