So I found a roku remote app in the win store and does a decent job at being a remote control for my roku. However, it also claims to be able to stream videos. Unfortunately only got the samples to work and it seems like it won't stream a file per set, it will only play a direct internet link to a playable file (so all YouTube is out, meaning the http link must end with a .mp4 or .mov which is fairly rare). I suppose if I can find a way to wrap my files in an http link then it should work. For the record it can't handle https so no drop box/gcloud/skydrive sharing links will work either.
Its a start!!