For some of my plugins (e.g. questionnaire), I maintain multiple release trees. My strategy is this:
- New features go into the next release of Moodle. So, if current release is 3.5, I create new features for the 3.6 release until the 3.6 is current.
- Bug fixes, security fixes, and valuable improvements (my decision), go into the current release and backported up to two previous releases.
At the moment, the order of versions on the plugin versions page is hard-coded, and matches the logic of the in-built available update checker: always prefer the most recent plugin version that supports your Moodle version. There is no current plan to change that.
In fact, there is an existing counter-proposal from the community that the page should only display the current (latest) versions for each Moodle version.
I can imagine the page could be made a bit more dynamic, e.g. showing a latest plugin version for each Moodle version, with a link/button like "show other plugin versions for this Moodle version") that would then load and show all the previous plugin versions.