Now that this is mentioned, I revisited WordPress' instructions page and it says: "Most domain names registered at WordPress.com have GDPR protection, which means registrant contact information is not visible publicly, regardless of whether or not the domain has Privacy Protection in place. For these domains, disabling privacy will not result in contact info being publicly published."[0] Does this mean the process doesn't really need it but they registrars require it for some odd reason? If they can work it out without disabling privacy feature to comply with GDPR, why can't they do the same for everyone?
[0] https://en.support.wordpress.com/move-domain/transfer-domain...
From the Domain Tools point of view the transfer should look like Old Whois Privacy LLP on SomeRegistrar transferred a domain to New Whois Privacy Corp on NewRegistrar