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Bert2005Flag for United States of America

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Is Windows Server 2016 Essentials worth using so close to EOL support?

OK, so I already know the answer. I am very familiar with Windows Server 2016 Essentials. But, Windows Server Essentials is a step over my head.

I know that 2016 is basically EOL early in 2022, but Microsoft is supporting it with security patches until 2027. But, you won't get updates and bug fixes or that is what I am reading.

Would it be stupid to do this or if I feel more comfortable getting a few more years out of my server with a setup I want?

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If your deploying a new machine I would take the time to learn the new version vs deploying an OS that is already outdated.
Most windows operating systems are not that different from their previous versions that it is a struggle to update your skillset.
Also keep in mind that technically to deploy an older OS you still have to buy the new version and software assurance (as that gives you the rights to downgrade) so that you can downgrade to the previous version since you cannot buy 2016 anymore (if you already have the license then that isn't a concern)

Security patches as you and kevinhsieh already pointed out is the biggest concern. They will still release security patches for Server 2016 until 2027-01-11 through extended support. (just mainstream support ends in 2022).

So as long as your sure it will not be in service past 2027 it probably doesn't matter either way. 
We didn't go the Essentials route when Microsoft cancelled the SBS line (former SBS MVP here).

We built a feature set based on the Windows Server stack and Remote Desktop Services that is vastly superior without all of the restrictions Essentials introduces.

If cost is a consideration, the SPLA the Windows Server licenses and RDS SALs. 
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There is no cost consideration as I am a Microsoft Partner and have tons of licenses. I just loved SBS, and I know that 2016 is that last one with the wizards, et. al. 
The Small Business Server product made a huge impact on Microsoft starting with its 2003 version. That's the one that took the world by storm surprising everyone but those on the ground deploying it into SMB/SME.

The Wizards made their way into most elements of the Windows Server Stack.

Now, instead of Wizards PowerShell makes for a consistent and simple way to set things up.

  • VM0: DC
  • VM1: Exchange
  • VM2: RD Broker/Gateway/Web
  • VM3: LoB/File/Print
  • Option: VM4: Dedicated Session Host
  • Option: VM5: SQL/Dedicated LoB

That's our default go to when setting up a Greenfield or when migrating.

We took a run at Essentials. The takeaway from that product was ARR and URLReWrite (Application Request Routing) that Microsoft uses in their public cloud among other places. We use that for a single WAN IP to several HTTPS published services such as Exchange, Remote Desktop Web and Gateway, SharePoint, and/or published LoB.

Other than that, it was a no-go for us. We built a Stack solution instead.