I didn't check the logs again to see if a DLNA event happened in them. Understanding DLNA events from the logs is difficult, usually. I can't look now but might get a chance later.
However, the symptoms you described; Playing Now being cleared for the Zone you were playing to (Media Room in this case), and just one file showing in the default Player Zone, is consistent with a DLNA Controller taking control of the DLNA Renderer (Music Cast) and either viewing the play queue, or trying to play something using Music Cast directly, or doing something which would indicate that MC is no longer the DLNA Controller for the Music Cast DLNA Renderer Zone. MC does monitor to see if another Controller has taken control of a DLNA Renderer it is playing to, and will release control if that happens.
Once that happens, MC will likely switch to the default Player Zone on track change, and the track it was trying to send to the DLNA Renderer will be placed into the Player Zone Playing Now list. At least that is what I have observed previously.
One way you may be able to confirm this is if you know for sure that the single track in Playing Now was that last track actually played, or the next track to be played. In the scenario I described it would be the next track to be played, not the last track that was played. Perhaps you can try to confirm that when next it happens.
I don't use the JRemote App on iOS, but do use the JRemote2 App on Android. That has settings called "App follows server zones" and "Server follows app zones". If the MC Server is set to follow the App Zones, and someone opens the JRemote2 and changes the Zone then MC will change Zone. That doesn't cause the problem for me playing to a MC Renderer, but it might playig to Music Cast DLNA Renderer. Usually though, MC handles playing to two or more different Zones (audio devices) just fine. But if the Music Cast App was opened on iOS, that may not be the case.
Honestly, the Recent Playing Now Smartlists are a bit of a mystery. MC manages them automatically of course, and it seems to create one when a change is about to be made to Playing Now, such as when a new track or tracks are added to an existing Playing Now list. I've also seen MC create one when I hit Stop, and when I hit Play after adding a bunch of tracks.
I used to think the list of Recent Playing Now's stayed for a day or so, but maybe that was only when I didn't restart MC. Just now restartnig MC cleared all Recent Playing Now's. That behaviour is confirmed in the Wiki:
https://wiki.jriver.com/index.php/How_Playing_Now_WorksBasically, it is a handy feature during a session, where tracks are being added to Playing Now, or perhaps a playing session involves selecting Album by Album to add to Playing Now. But it a little mysterious for me to rely upon.
That's why I tend to build Playlists rather than building a list in Playing Now, if I am concerned about keeping the list. Then I just play the Playlist, and add to it if I require. Playlists are always saved and retained, no matter what else I do in MC.
If I do spend a long time building a list in Playing Now I might save it as a Playlist every now and then, just in case I get called away, have a power failure, a PC lockup, or make some mistake that could mean I lose the work.