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What we would miss and what we would get if upgrading the JIRA version higher?
Our JIRA setup has many automated and customised issues, which we wish to keep.
Could i create trial with Advanced Roadmaps for demoing it to others?
You can trial Advanced Roadmaps for DC and adjust the permissions so the Plans view is limited. When moving to Cloud, be sure to get a Jira Software Premium subscription or higher.