Unlike snapshot releases, milestone releases are tagged and published
in Maven Central, so I don't see any issues with upgrading to 2.0.0-M2
immediately. In practice, if a Commons FileUpload v2 API did change
between now and GA, it wouldn't be too much work to adapt the few
plugins that consume it. We routinely adapt small sets of plugins here
and there when there are breaking UI changes.

It would be nice to see someone explore the details of removing
Commons FileUpload entirely. Most of the Jenkins APIs that refer to
Commons FileUpload are in Stapler, with consumers in core and plugins.
A good starting point would be to reimplement Stapler, core, and at
least one plugin without Commons FileUpload. That would provide a
broad range of producers and consumers to validate any API changes.
The Testing Done section of
https://github.com/jenkinsci/jenkins/pull/5174 highlights the main
consumers throughout the ecosystem.

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