But my new GM (real Boss in the sense of my Manager thinks.. lol) said that it's my install and to do it my way, so .. here we are.
she wants to see what I can do.
Then purchase 2019 and cals for it, if you want to downgrade (for whatever requirement) then you can do that. But setup Hyper-V on the hardware (assuming it has to look like Windows) with a GUI and then create a VM to run the site.
Don't forget Dustin - these are restaurants... IF he sets up Hyper-V, he will likely have to do it from within a base Windows Server install so he has a console to work from.
It's unlikely that there will be an "admin" workstation for him to use to manage this server in the future.
You can opt to choose a GUI when you install server 2019 hyper-v. . .