I usually wait until closer to the season. I then also try to get retention and very politely say 'look, I'm not dumping you but you got to at least help me out with some credits to bring that price down". That usually pays for at the very least half of it and then I ask for free pay pay channels to make my other half happy and they ALWAYS throw me some free Showtime to shut me up. Of course with ATT now running the show they may be tightening their belts to pay for their investment.
...Is there anywhere on the DTV site that tells when your contract ends?