I am a 25year windows server admin. Yes Server Essentials I am very familiar with it And all of its predecessors… you don’t mention which version of server you’re on. You said I’ve been running since 2010.soooo leads someone to believe you’re still on 2008.
yes a security issue the moment it turns on. So you’re on server essentials in 2019 then great you’re supported until next year. 
Then run haos in a Proxmox VM and run a second VM with whatever your favorite flavor of 'nix is… Or windows or whatever. You will be much happier and tear your hair out much less. That install on Rpi os… You’ll be fighting it at least every other month. I loved away from supervised on a pi 4 for the same reason.