I'm looking for insight on how you handle storing documentation. I would love to be able to store user-facing documents with my roadmap versions.
Just have a look on the Documents add-on for JIRA. It may fully fill your needs. See https://marketplace.atlassian.com/plugins/com.stonikbyte.jira.plugins.project-docs-plugin
JIRA can only associate attachments with issues - fraid it can't extend to releases or projects. However, Confluence is pretty good at it and can be integrated indirectly with JIRA. This might be worth a read:
https://confluence.atlassian.com/display/DISC/Using+Confluence+for+professional+documentation
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