We need some clarification as to your issue here. Can you please share a screenshot of your Watched Folders from Roon → Settings → Storage?
Are you having this issue with *all *local content in your library when using the Windows Remote, or is it specific to your playlists? Are these .xml playlists that are failing to appear?
I’m assuming above that you mean your RoonServer machine is connected via ethernet. What about the Windows machine? Are they on the same router? What network equipment is in your setup other than the router?
Once we have some more information, we can proceed from there.