Our uni has been on Confluence Server for over 10 years. We're now assessing whether we want to go to Cloud, Datacenter, or move off of Confluence to another solution.
key questions would be the amount of users you have (DC has quite high the first tier, thus it is more suitable for larger organizations), what sort of plugins you have (to check whether there are cloud/DC versions of those) and most importantly - if you do have any integrations or customizations in your server version as those will be a bit of challenge to transfer to Cloud (sometimes :) ).
