Thanks for taking the time to share your experience and highlight some of the pain points we might encounter in a move to the Cloud version from server. Your honesty and openness is appreciated.
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I saw mention that you had looked at Data Center but weren't sure it would fit the budget for your organization. Given that you already have a Community license for Confluence Server, I wanted to make you aware that Atlassian also offers free Data Center licenses to qualifying nonprofits. Details are on this article and the process for applying is very similar to the process your organization already did for the existing Server license. Hope this helps!
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