I don't care how much of a Windows fanatic I was I'd never even try to use the GUI of the client version to configure the a box as a Docker server remotely. I don't know what to expect from that other than frustration. I'd definitely use Linux myself but if someone asked me to use Windows I'd still just enable the OpenSSH service instead of RDP and use the Server version if possible and if not at least set up the auto update schedule to the early morning like I would on the Linux box.