Dear Morningstar, I was trying to understand your problem and specifically what you mean by "playing random files in a folder" - how do you actually randomize them, and for what purpose?
And most importantly, but very OOT, from your screenshots I understand that you keep your music in the default "This PC" locations (in C:\Users\<yourusername>), which is IMHO very bad practice. When running Win10, all user files in default user locations (Documents, Music, Pictures etc) should be considered as at risk and potentially expandable if a Windows Update goes wrong. Thousands of such cases have been reported and more people are still searching and/or mourning for their files. The best practice is to reorganise your folders so that your personal files are outside C:\Users .
This is one of the main reasons I'm staying away from Win10 for the foreseeable future (a few more years by god's will) and I also advise so my dearest friends. As I said, very OOT but critical for our mental health :-)