Posting on behalf of a non-profit I help out at. They currently have an on-premises Windows Server 2012 R2 Essentials install. They're close to hitting the 25 user limit. Upgrading to a Standard release of Windows Server is the only feasible option. Does anyone know if it will be possible to upgrade directly from Windows Server 2012 R2 Essentials to Windows Server 2016 Standard? Money is a major concern, so they're keen to avoid having to pay to upgrade twice (either 2012 Essentials -> 2016 Essentials -> 2016 Standard or 2012 Essentials -> 2012 Standard -> 2016 Standard).
I know that some well-meaning people are likely to suggest moving to a Linux server, but we've had to rule that out. I'm a Linux person and would ordinarily recommend it myself, but they need to be able to run some proprietary Windows only software, and they also need to be able to do some maintenance themselves. Linux has been considered quite extensively but it's not a viable option as I can't always be on hand to help and their other computers and experience are exclusively Windows.
Thanks in advance for any information. I've been unable to find anything online about this particular topic.