Thanks for the file, I've sent over to our engineering team to look over, and to gather more information.
Semi-off topic/experimental data.
More observation about the behavior about our system and DRMed iTunes media
Using a song that was purchased from iTunes, it had the extension of .m4p. However, when I changed this extension to .m4a; the iTunes server was able to detect the file, and stream it to my iTunes client. In conjunction with the information from this thread
I was able to make the iTunes server read DRMed files. However, content information, such as album information was not passed over to the iTunes client.
Please note while this information is for personal and legal uses only. Users must comply with all applicable local laws and regulations with regards using DRM media.