Synced Playlist Not Updating Correct Songs

I like to track the songs and genras I listen to over time so I have a playlist for my top 100 songs from the past 15 days.

It doesn't seem to be updating every 24 hours like I thought it would. But more importantly it is loading in the wrong songs or forgetting some completely.. even though my "Top 4 weeks, and custom 15 days shows it properly... the playlist is wrong.