Note this only applies to "full power" stations, and that repeaters are not required to do this now. I think their deadline is with the cable deadline in two years.

Where my Mom & Dad live in rural Central Oregon, they still get their TV from analog repeaters. There are no digital stations within range. My guess is they will probably make the switch as it becomes financially convenient, i.e. when repeater components break and they can't get analog replacements anymore.