I just found out that MyMedia (via the PlayOn channel on my Roku®) now picks up my Windows Media Player playlists! So, I can play my music on the receiver in the family room, turn on the stereo in the office and have my playlists playing throughout the house.
I'm thinking the problems I had last week were all for the better.
Listening to my "Little Martha" playlist right now (yeah, you got that right, I have a playlist with just different versions of "Little Martha" on it; one of my fave Allman Brothers songs).
I got my first Roku years ago from Woot for Netflix. Then there was Amazon, then HBOGo, then EPIX! and...and..and... I tried for hours and hours throughout the years to get my playlists on my computer to stream to the other room. I had some of those senders and receivers, but I hated all of the extra wires and having to turn them on/off. I was able to access the media files, but not the playlists (and when you've got over ten thousand songs, a playlist is a very nice thing to have).
I was very happy this morning to discover this updated option.