We had a very similar problem with RadioBOSS.
In our case, the issue was related to the hourly playlist change and scheduled events. Under certain conditions, RadioBOSS could receive two commands around the same time. This caused either two songs to play at the same time, or the first song of the new hour to be skipped.
The problem was solved by changing the way the new hourly playlist was loaded.
We stopped using a nested runevent command for the “Load New Hour” event and instead loaded the new playlist directly with a command such as:
run PlaylistGeneratorPro.exe -preset=Day -out=D:\PlaylistTemp\new_hour.m3u8
So he generates first the playlist for the comung up our , output is a specific folder with alway the same name ex. new_hour.m3u8
Then the news and other information runs after the latest jingle for the new hour he get gets command
load D:\PlaylistTemp\new_hour.m3u8
We also made sure that the new playlist was loaded as regular playlist tracks, not as scheduled tracks, and that overlay playback was disabled.
After changing this, the problem disappeared and the hourly transition worked normally again.
I would check whether two scheduler events, playlist load commands, or scheduled tracks may be triggered at almost the same time.
We also occasionally had RadioBOSS skip a song somewhere in the middle of a playlist, not only during the hourly change.
Interestingly, this problem also disappeared after we changed the hourly playlist from scheduled tracks to regular playlist tracks and simplified the event chain.
So in our case it seems that the way the playlist was inserted by the scheduler may have been part of the problem, even when the actual skip happened later and not exactly at the top of the hour.
Since making this change, we have not seen the random skipping issue again.