“What are the challenges with migrating from an on-premise solution to a cloud-based solution?”
On the nuts and bolts side, with an onsite solution, as long as your in-house network cabling isn’t extremely old or damaged, you shouldn’t have to worry about connectivity issues. And, any issues that may arise related to equipment, you are able to address by sending someone to the physical location of the problem. Once you migrate to a cloud-based system, I think the larger issue is really trust. Being able to trust that the third-party, which is now storing your data, will keep it both secure and reliably accessible.