Go ahead and buy licenses as a show of support, but I strongly suggest that you exercise the converter scripts in both directions, partially to know what will cause them to fail, and partially to have an option when the vendor misbehaves.
Red Hat offers a "no support" server license for $350/year, which is the lowest licensing tier. Tiers with more capability and support are available for $800, and $1300.
https://www.redhat.com/en/store/red-hat-enterprise-linux-ser...
Oracle has a larger range of tiers. The "no support" license is $120/year. Tiers with more capability and support are available for $500, $1200, $1400, and $2300.
https://www.oracle.com/linux/
Oracle Linux can be used in production without a paid license of any kind; Red Hat Linux cannot be used in this way for large deployments (excepting the new 16-seat license for a developer account).
Red Hat is aggressive with software audits; I have seen one.
Both Oracle and Red Hat now have complete toolsets to convert support between an installed CentOS/RedHat/Oracle OS.
Red Hat can now convert an installed CentOS or Oracle Linux to RHEL; previously a wipe and reinstall was required ("have fun reinstalling your system" is still on Oracle's CentOS site). The description looks much more thorough in replacing all possible packages with Red Hat versions:
https://access.redhat.com/articles/2360841
Oracle does not replace CentOS or RedHat RPMs in their conversion (AFAIK), so it is much less violent on the platform changes.
https://github.com/oracle/centos2ol
https://linux.oracle.com/switch/centos/
https://blogs.oracle.com/linux/reasons-for-switching-centos-...