So here's how you can move your library from either Win7 to Win10 (did this already once w/these notes), Win10 to Win10 (also did this with these notes) and hopefully Win10 to MacOS High Sierra (doing this right now as i write this).
--Some Background--
Anywho I just re-added a late 2012 Mac Mini (only a core i5 one but for just $300 w/kb and touchpad!!) to my setup since i missed native Garageband after using a Lenovo X220 as a hackintosh (not bad but not a real mac). After being very annoyed with Win10 and how it loves to just reboot at will after updates and me trying to access media away from home to then come home and see.. yea, my little pc is stuck on the bitlocker password screen and in turn still at pre-boot (UGGH!!! whole series of blogs could be written about how Microsoft's enterprise support/qc of updates is PURE SHIT!!! see reddit's sysadmin for the joys..) decided the mac mini was best machine to use since its always on and stays pretty quiet when running / hosting plex in the past.
So moving on to the actul process. Full official notes over here at plex's site too:
https://support.plex.tv/articles/201370363-move-an-install-to-another-system/
Migrating your Plex Media Server library to a new system, keeping metadata, collections, etc
1. Disable Emptying of Trash after every scan under Server Settings > Library
2. Install Plex on new computer.
3. Open Plex and then sign-out and finally exit/quit out of the server so it fully stops on the new computer.
4. On the old server we are moving away from, stop plex and exit (I recommend this)
Then in your file explorer/finder, go to here (depending on os)
Windows
%LOCALAPPDATA%\Plex
Media Server
OSX
~/Library/Application Support/Plex Media Server/
cache, crash reports folders,logs and updates (big and tons of files!)
6. Now copy these files back to new system in the same folders. After they finish copying, reboot the new server. This is required on OS X.
7. Now start/launch Plex Server on new system and open Plex Web App
Content should be shown but won't be playable, now we need to sign out and back in (related to valid certs,ssl/secure connections) to the Plex Web App.
8. Now after we are signed back in, Edit your libraries; update locations and ADD the new locations while still keeping old ones there for time being. Do this for all libraries; do one at a time due to time it takes!
The library will update itself once you edit it, if not initiate a Library Scan from menus.
9. Once everything is scanned, complete, verify media is working and content is accessible; remove old content locations in each library.
10. Lastly, maintenance!
RE-enable "Empty trash automatically after every scan"
Empty Trash for server
Clean Bundles and wait a few mins after window appears
Optimize database for server
- this process has been verified to work migrating from Win10 to MacOS High Sierra. :) 4/12/18
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