Other than some plug-ins not being available for Jira Cloud, and that the UX will be different, what are the major functional difference between these two versions of Jira?
https://confluence.atlassian.com/cloud/compare-atlassian-cloud-vs-server-744721664.html is a good comparison.
It does lean towards Atlassian's drive on getting everyone on to Cloud, which I could argue with. But have a read of that and feel free to ask us questions (and for opinions if you want them, as I've already mentioned one of mine)
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