I think as a Community we should focus on to push Jakarta EE forward with the Speed needed to stay update with new market expect and needs.
I know that backward compatibility is desirable and is an important thing and I think we should keep that in mind for future releases but, the situation we are facing now was not created by us or by Eclipse Foundation.
So, I think we should invest effort and time to do the necessary changes to move from javax.* to jakarta.* (going for the big bang approach) and make clear to all that, to run Applications keeping the compatibility, the user would continue to use Jakarta EE 8 and, of course, to keep update with this new project momentum and receive new features, everybody should make an effort to migrate their Applications to run on Jakarta EE 9.
Maybe we should had a strong commitment to offering help (for those who needs it), writing blog posts, books, making videos, doing online code review sessions and help anybody that face problems with that migration process.
If we detect that there are old dependencies that, for example, doesn't have code available anymore or not have the original maintainers, maybe it's the right time to face that problem and fix it (if possible). Otherwise, we'll keep facing problems related to this package limitation thing on the future.
To help others with the same migration issues that will come, we could create an GitHub repository with common problems facing by the community during the migration and with the solutions taken (or simple put the link to Stackoverflow question).
Silvio Silva