Last night I fired-up the WHS 2011 rig to BU the Main rig data again. After the WHS rig settled down it wanted to install 12 "important" updates, I was happy to see this as it appears to me that WHS 2011 will keep installing important/security updates even though the "Mainstream Support" date has come & passed. There is no "Extended Support" offered for this server OS. I'm hoping that since WHS 2011 is built off of Server 2008 R2 these updates will continue through 1/14/2020. Not wanting to shoot my big bucks for a new Server Essentials OS yet.
Oh yes still updating, even XP will be updated until 2019 thanks to the PosReady packages. It lacked only two things WMC and the deduplication. But given I solved both the problems thanks the WMC and Hyper-V packages, and given it still works perfectly if connected to W10 machines, there isn't absolutely any need to replace it.