Track List feature offers "Series" option: https://manual.djsoft.net/radioboss/en/using_track_list.htm
It does not advance automatically, you need to create another event that moves it to the next track.
If nothing is playing, and it's time to start an event it's logical that the event starts playing. That is, you have scheduled a playlist for 12:00, and nothing is playing. Everyone would expect that when 12:00 comes, an event will start and play. Otherwise it's a weird behavior - scheduled...
In this case it doesn't know if specified path is a file - so it treats it as a folder.
It is possible technically of course, but before implementing it we need to be sure there's a demand for such a feature from other users.