I would expect PlayIt Live to run fine using music stored over the network on another server. This must be stored on the same network over an ethernet connection to ensure the audio is available at all times. Using tracks stored in the cloud or an external server over the Internet is not recommended or supported.
Ensure that you are able to access the files directly using File Explorer before trying to add them to PlayIt Live.
I would recommend copying the file to the local disk and loading it into PlayIt Live there. This way it does not need to be loaded directly over the Internet.
You could make a local copy and use Microsoft's "Sync Toy" to make the local copy on the PlayIt Live machine the same as your "master" copy.
While Microsoft seem to have discontinued support I still find it useful.
Is it possible to import Tracks into Playlit Live from an external Server?
I have a Linux Server where I would like to store my Music on and then import it into Playit Live. Is that possible?
I already tried mounting the folder from my Server into Windows Explorer and then select the folder/drive in Playlit Live but this just causes Playit live to crash.
Thanks in advance!