Okay i figured out myself, i was using the wrong path for the Collection. When the files of the Playlist were were also in the collection the counting started to work.

Its been literal years that i wanted to see this feature working, i didnt expect it to be such a simple thing, the main problem is that its not intuitive at all, a label or something saying "songs from the current playlist will only increment the playcount if they are part of a collection" would have helped for sure.

I will leave this post here just in case anyone has this same issue. I dont see a button to close it though, so i'll leave it open.

I have a playlist that i have been using for some time (i've using it even before strawberry existed, i created it with clementine) for some reason the play count/skip count never worked (not even in clementine)
is there a known reason for this? i already tried changing many different settings but nothing made any difference
All files are stored locally, i thought it should just work but it doesnt
Most of my files are MP3

I tried finding the problem myself in the source code, and i believe it perhaps be that the id of the playing songs is always -1 or IsLocalCollectionItem is always false:
https://github.com/strawberrymusicplayer/strawberry/blob/c6e42e10320da4dbe832e2973c181328de34b021/src/core/player.cpp#L464

but i'm not sure. either way, i tried deleting all configuration files and importing the playlist again, it still does not works