After a month, I have spent $36.70 on iTunes shows. They are:
Multipass to The Daily Show (16 episodes, still running)
Multipass to The Colbert Report (16 episodes, still running)
One episode of The Cobert Report before I got the multipass
Heroes episodes 1-5
South Park WoW episode

I also bought The Office season 1 and 2 on DVD, but have not watched them yet, costing me $69.26.

I've also been attending the showings of Battlestar Galactica at the Alamo Drafthouse. They are free to get in to.

Beyond that, I've watched a lot of video netcasts, including DL.TV, Command N, Ctrl-Alt-Chicken, Diggnation, and Cranky Geeks. All of them in the same Front Row interface that I use for the iTunes shows.

Right now the shows I miss are Smallville, Mythbusters, and just general information shows like Discovery tends to air. I did dig out the Voom box, but have yet to hook up my ReplayTV again. The local PBS station does broadcast in HD, so I've caught an episode of Nova that way.

For now, I think I'm comfortable with the arrangement I have. I'll probably look into an HD tuner PVR solution for the Mac Mini to record over the air shows, instead of investing in equipment with DirecTV or Dish Network. I may look at the price of the packages Time Warner has, but odds are the channels I want will be all over the place, resulting in an $70 bill. While I did spend more then that this month, the Office DVDs and the multipasses will carry me into November.