download vlcportable and unpack it to a folder
for a set number of plays
vlcportable --input-repeat=10000 track1.wma
for "looping", start vlcportable and then choose the playlist option and save it...
then you can command line the playlist by
vlcportable --loop playlist.m3u
--random plays files randomly forever.
--loop loops playlist on end.
--repeat repeats current item until another item is forced
you can create a sh/bat file too... then maybe put it in startup?