I'm planning on building a server for Plex instead of just using my computer to upload to Amazon or Dropbox, so how clean of a migration process is it to move from Windows 10 to something like Windows Server?
It'll probably be Windows Server 2016 for when I actually do any of this (from what I've read, Q3 of 2016 is when it's scheduled for full release) and I want to be sure that I can migrate the Cloud Sync setup over to it (so all videos would then be moved to this new machine).
I want to avoid having to reconvert and reupload all 1.5TB of my videos, though the Cloud Sync would end up just being a redundancy with the server running 24/7.
What would I need to do to ensure that the process of transferring things over works? Does the drive letter matter?
I have already carried a Cloud Sync setup through a Windows install, but that was still on my main PC so everything matched up the same and it went without a problem.
On a sidenote, is it possible to move from Windows 10 to any variant of Linux without any problems with Cloud Sync?