I would never upgrade until it is absolutely necessary. And, I know that many people don't have a server setup and, thus likely, no VMs. There is really no excuse if you're not using VMs if you are using the product on your machine. Virtual machines give you MULTIPLE advantages over running directly on Windows. Checkpoints would have saved you a lot of time testing the new program. Yes, it would good, almost necessary to have a real server, yes you would have to purchase Windows Server 2022 Standard or at least 2019. I am believing that 2016 would but I know that a 2019 and 2022 license would give you licenses of two VMs. Yes, you would likely need someone as an IT to set it up or James but it is a physician's office and your data is paramount.