WIndows Storage Server 2008R2 Essentials is basically just WHS2011, but with 25 users and computers. It's also OEM only, and much more "regulated". It's very hard to find without using Technet/MSDN, IIRC.
And .... WHS isn't dead. In fact, the entire WHS2011 code is *what* makes Server 2012 Essentials what it is. Literally.
Also, end of mainstream support means that it only gets critical security updates, IIRC. And that will last as long as Server 2008R2 is supported.
Mainstream support for 2008R2 is Jan 2015... while extended support (aka critical updates) last until 2020. So that's a good long while.
And Server 2012 R2 *is* Server 8.1. As Server 2012 is Server 8.
Also, the "Essentials" Role (aka the code that made WHS) will be available on Standard and Datacenter versions of Server 2012R2, IIRC.
And I'd wait for Server 2012 R2 Essentials, if you want to go this route (which isn't a bad idea). Namely, because it handles bare metal restores better (can create a recovery disk from scratch, and may integrate drivers, as well as supports PXE, aka network booting of the recovery image).
remember whs 2011 is based on server 2008 R2, while I can't say this with certainty, but I would think as long as Server 2008 R2 is supported, we should be ok when its comes to security patches through 2020, if I'm wrong you have a good two years and a few months, lol.
You are right that Windows Server 2012 Essentials is a good chunk of change! It does have a dashboard, Client Backups, Shared Folder management, and Remote Access, the same as WHS does. In addition to this, it also provides a DNS server, and VPN server for remote connectivity to your network. The downside to 2012 Essentials is the following:
It makes your clients join the domain when you install the connector
In order to enable remote access, you must install a valid certificate
It statically sets all connected client DNS addresses to its IP address
File transfer rates to the server are initially quite slow
If you are willing to put in some extra time, all of these issues can be worked around as follows:
Skip domain joining when installing the connector
Create a self-signed certificate and enable Anywhere Access
Keep services from setting a static DNS entry for the server
Disable SMB signing to speed up file transfer rates
Another thing to keep in mind is that Windows 8.1 will likely be released in October and Windows Server 2012 R2 at around the same time. The upgrade from Windows 8 to 8.1 will be free, but I am not sure about the server versions.
If price is your biggest obstacle, then Windows 7/8 and a PC backup solution will be cheaper than a server OS. WHS 2011 is not going away any time soon. It is still available for OEM pre-installs until 2025.
I think that your choice of OS depends on the features you would like to have versus the ones you must have. I choose Windows Server 2012 Essentials because I want and use pretty much all of its features, except media streaming and VPN. Desktop solutions are always much cheaper, but you may have to spend more money or a lot of time trying to get other features you may want, such as remote access/media streaming, PC backups, centralized user management, VPN, DNS server, etc.
