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Do you generally trust season passes to work properly?

Yes. I barely use anything else, I get all the programs I want (with a few irritating exceptions) and I almost never record anything manually.

The irritating exceptions are when the DirecTV guide data isn't good enough, and that's because Tribune Media's data isn't good enough and that's because the channel doesn't provide good enough data to them. In particular, this means USA Network doesn't provide correct First-Run/Rerun information for its original shows, so I have to pay attention to when the Monk and Dead Zone seasons start and reenable the Season Pass, at which point I get the new shows and some reruns, especially when they decide to run a marathon. Comedy Central used to be this way, too (you'd get like a hundred South Parks and Daily Shows a day) but they seem to have fixed that now. (Actually, they were even worse; the TiVo couldn't even tell if it was the same episode, so it'd record the same episode a dozen times.)
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Bitt Faulk