Every time I open a play list and the player is set to Shuffle Randomly, it plays the same items in the same order.  Yes it DOES skip randomly through the list provided, but it plays the same randomly selected items in the same order every time.

As a software engineer, I would suspect that the random number generator is not being randomly seeded when the application starts up or with the current date time, or it is being seeded with the exact same number (0?) every time.  As this is easy, basic, software 101 coding it is something that can be easily corrected within your applications to give us a truly random shuffle selection every time we open the application. 

Create a FILO (First in Last Out) list, an array of 100, 1000, or 1000000 items and populate it as items are selected, randomly pick another item (that is not in the list) and the newly selected item to the list, play it, and remove the last item in the list.  Rinse and Repeat for ever and ever Amen.  Easy as pie (355/113).