They did in DP191, but it wasn't the same.Im kinda glad they didn't play it after Kanto. Then the song never gets old and has a special meaning when you listen to it since its not always being used.Tears After the Cloudy Weather was a such a good and emotional piece of background music. It's a shame that they never really play that track ever again, after the Kanto portion of the anime. Though, admittedly, there's not much places for it to fit appropriately in the current anime... Just goes to show you how much the series has changed.
My favorite times this song played has to be the first episode, Butterfree's farewell, the time where Satoshi and his Pokemon were warming each other up in the blizzard, and Ai's death in the CD Drama. All were really tearjerking moments.
It never does get old hearing it though. It does feel special. :)