I do not really get and understand what you are saying.
And it ALL depends how your programs and scripts do looks like and how your media libraries and tracks do look like.
You provided many screen shots, but they do not tell much, as I don’t see your script or history.
I also only see two PlayCounters (19 and 36). Two numbers, which doesn’t tell much.
Because I can only see one filter and one script history setting. You probably still use a global history, multiple media libs etc.
All this influences the tracks and when they are played and if some tracks are skipped.
You might use the Script Test function to understand when a history entry is hit etc.
The tutorial video about the history also explains, this.
The more options, histories and filters you use the more dependencies do you create.
What script-line mode are you using? Random, LeastRecentlyPlayed, LeastTimesPlayed?
How big are your media libs?
However, the LeastTimesPlayed mode of course has a bias towards the PlayCounter (that’s the purpose of that mode).
So overall it can get very complex and isn’t simple to answer.
But ProppFrexx doesn’t ‘like’ songs more than others
it strictly follows the rules defined.