A restaurant that I frequent, here in Edmonton, has been playing the streaming Internet radio station 57chevyradio.com a few times lately. Today, a local ad was automatically inserted a couple of times for a hospital lottery being run in Edmonton. By the "station", not by the restaurant. Never heard that being done before, but I don't normally listen to Internet radio stations.
Coincidentally, yesterday, I was doing a 25 Years Ago item on Pelmorex, who had just begun heavily marketing their individually-tailored satellite-delivered national radio networks. They had adapted the technology they were using for their own specialty TV channel, The Weather Network. Local weather forecasts and conditions are automatically inserted throughout each hour. Their radio networks inserted local content read by their national announcers, and were being sold as cost-saving measures at a time when about half of the private radio stations in Canada were losing money.