Your proposal sounds great to me, and thanks for volunteering to implement
the changes. I think a late-2022 timeline (sometime after 2.375.1 has been
released) makes sense—if there is some advantage in waiting longer, I do
not get what. The only likely drawback for plugin maintainers who
deliberately wish to stay on a pre-2.361.x baseline is that Dependabot (if
configured) will offer `plugin-pom` updates that fail CI builds, which is
not so bad since the release notes will explain why, and the PR and its
replacements can simply be ignored indefinitely. (And of course you will
not get access to new stuff in the toolchain, but that seems fair.)

Independently of that, we can consider switching the default JDK for
ci.jenkins.io `buildPlugin` from 8 to 11. Even if your plugin supports
older baselines and Java 8, running the build on JDK 11 is typically fine,
since `-release 8` will ensure the right bytecode and even prevent the
infamous `ByteBuffer` problem. The likely issues: you will lose Java 8 test
coverage (while gaining 11 test coverage, which is more important!); and
occasionally some tool like `javadoc` will be stricter (in a way you ought
to fix anyway though you might have preferred to take your time).

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