Here are some of the questions that have been raised at OEM events over the last few events... as we still have a few more coming up I'll add new posts covering these. Please note that none of these override anything in the EULA or Product Usage Rights documentation, if they have updates that are different to the licensing related answers below, then they are the source of truth.
What are some of the differences with licensing Between Windows Server 2012 R2 Essentials and Windows Server 2012 R2 Standard and Datacenter editions?
The main one is that Essentials includes the right for a maximum 25 users as part of the base license, which cannot be increased to a higher number. Standard and Datacenter do not include any CALs, and they need to be purchased per user or per device, whichever is better for the customer.
If using Remote Web Access to access your WIndows desktop from a remote location, this is covered by the Essentials license. If you use the same functionality via the Essentials Experience in Standard or Datacenter, you need RDS CALs for those users, even if they are just access their desktop PCs remotely.
Why Standard Instead of Essentials?
The main reasons are either going to be the number of users, or alternatively because you need multiple virtual Windows Server instances.
Can I get granular with the Essentials Experience role's features?
You can choose which features you want to leverage once the role is enabled, but certain roles such as it needing to be the holder of Active Directory FSMO roles, for example, needs to be maintained. You can choose to not leverage features such as Microsoft Online Services integration, client backup, granting RWA access etc, but the underlying pieces will still be there.
Is there any more information about out of support operating systems and the impact on financial institutions?
Yes, there are a few of them so far.