1) Always recommended to upgrade to the latest version as it would consists all the latest bug fixes. 8.5 is the latest JIRA Software Enterprise Version . I'd suggest you maintain (n-1) version - that's my personal strategy to keep one version older than the latest.
Note : Read the release notes to ensure what changes are made with the new version - what new functionalities can be expected and what have been removed .
https://confluence.atlassian.com/jirasoftware/jira-software-release-notes-776821069.html
2) Some of the major things to take note of are as follows ;
- ensure your current plugin versions are supported by the new JIRA version you are upgrading to . If there is a higher plugin version - ensure that you do it.
- always take a backup before you do an upgrade.
- if you are not confident about upgrade , do an upgrade in your test environment first , it helps you understand changes in JIRA
- if you have any customizations , ensure you know where they are so that you can reapply them after upgrade
READ RELEASE NOTES
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