“What are the challenges with migrating from an on-premise solution to a cloud-based solution?”
If your current solution is a small one – say just a few displays at or near the same location – moving to the cloud should be trivial. You will primarily be just copying content from a local repository to the cloud. Depending on the solution chosen, if your content is already stored in the cloud, you may be able to simply define and configure remote access and be up and running in no time at all.
On the other hand, if you are migrating from a substantial on-premise solution, the challenges will be greater as in addition to content relocation there will likely be networking changes possible along with security issues to resolve. Scheduling content may be different depending upon the cloud provider’s CMS. Nevertheless, a cloud solution may be worth the effort in the long run as these solutions are likely to prevail in the marketplace with potentially the lowest cost per display while offering the latest features.