I, and waiting for RadioBoss to work in the cloud, have found a solution that can help you.
I use EasyTanda, a program unrelated to RadioBoss that creates advertising spots in m3u format and that I later program on RadioBoss. All this is done in the cloud, with which very comfortable programs from the PC of the commercial and the speaker does not have to touch at all the computer of the air.
Anyway, why not programs on the PC of the commercial and give the route of the cloud to save the commercial batches. The only problem may be that this pc has to be continually lit so that it updates each day.