Thinking of switching to Win10 on my T3610
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Only ever run Plex server on Windows machines so I can’t speak to the differences in W10 and Ubuntu.
Plex on Windows is super easy, everything graphical. Just install Plex server, make config changes in the web UI and manage your library/files in Windows Explorer. Download, drag and drop, etc.
I am. Was on Ubuntu VM in hyper-v. Then switched to win server 2016 with geforce hw accelerated. And then switched to Ubuntu VM again in proxmox with hw geforce accelerated. There are docs on Plex site how to move all your library. You just need to copy one folder.