I found after I had updated to the latest iTunes 184.108.40.206 (on Windows Platform) that my smart playlist played on iTunes, not my iPod, would not update the last played date nor the play count.
I quickly checked the “crossfade songs” option and I did have it turned on, after all who needs to listed to 5 seconds of fad out, turned it off.
I played a song in the same playlist, and it started to correctly update the last played date and play count. I turned it back on and it continued to work correctly.
“crossfade songs” is under edit, preferences. choose playback and uncheck the “crossfade songs” check box.
I found that it quits working again, if some menus or pop ups are open during playback. arg!
So I am guessing they got something to fix there. I can recreate the issue by showing the about while “crossfade songs” is checked and playing a smart playlist. The Up Next window does the same thing. I have also restarted iTunes, with crossfade songs checked the issue continues to reoccur.
I have also been able to recreate the issue with the mini player. I have also had the issue occur with “crossfade songs” turned off, but I need more time to test.
apparently issue in on MAC also