Official comment
Have you allowed iTunes to play with the other kids?

I am changing over laptops. Running iTunes v12.7.4.76
Running Rekordbox 5.2.2. Was running 5.2.0 on prior
The Rekordbox advanced is pointing to my iTunes library XML file. My iTunes advanced is pointed to the folder that contains the iTunes XML file. iTunes doesn't point to the XML direct, it points to folders.
I screenshot the pathways comparing the two computers. I downloaded 2 new songs (purchased from iTunes). It won't show up, I have to drag and drop.
This also means my folders aren't dynamically updating as well
Have you allowed iTunes to play with the other kids?

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I have had this problem - I have clicked the box - but my iTunes playlist shows but Not the most recent .. any idea?
Have you checked that rekordbox is opening the correct iTunes library file?
If you're using the Sync Manager within rekordbox, uncheck iTunes from that sync function, close Sync Manager, click the refresh icon beside the iTunes listing on the tree, then re-enable iTunes in the Sync Manager again if you want to continue using it (but I don't recommend it, I find it easier to do everything manually).