Hi @BerntJulian and welcome to the user forum, glad you could join us here.
Thanks for looking ahead. Rewriting is fine - the result just ends up as GPL + EPL exception like the rest of GeoServer. The ability to use these tools is part of why we like free software.
The GeoServer project would also really like to migrate to the next version of EE (JakartaEE and Tomcat 10). For more information on the challenge see GeoServer 3 crowdfunding (and the Q&A section near the end with pictures). For our own GeoServer 3 planning we have focused on openrewrite but are keen to learn about your experience!
aside: The real goal here is not so much JakartaEE and Tomcat 10 as it is updating to spring-framework-6 and ensure GeoServer is operating in a supported environment.