I have had issues with the EPG and Timers for years and . . .
. . . have gone round and round with DISH. Tribune Media is also Zap2It the online gaming/entertainment provider that supplies the games and whatnot on DISHhome in addition to the EPG AND not TVGuide as the bug (logo) would/has led you to believe. I have spoken with TVGuide and they have no idea why their logo is on the EPG since they do not supply info for it. Even though DISH says they do. But do have a channel in the lineup. Free advertising?
For years I supplied volumes of proof from TVG, TitanTV and the stations themselves that proved that Tribune is the worst source for information. When and IF the information is "correct" things tend to work as well as they can. BUT it is wrong more than right. DISH would blame the stations for last minute line up changes that they could not physically keep up with. Each instance this was not the case. Just plain laziness on DISH's part. Especially when episodes are not marked NEW as they should be, which is a prime ingredient for name based recording. In the beginning before they made the timers a little more sophisticated I was missing everything AND called TS every time it happened. They got really tired of me. Since they have changed a tad, I have had to learn how to use the shortcomings of the EPG and the Timers to make it work. One really stupid thing is that the timers also don't take in consideration that if the program prior started early that is will most likely end early, and will not let you set a following program to start early enough without stepping on the previous one. Even though it won't, it acts as if it will. Have spent many hours "shaving" minutes to get things that should work that won't.
I watch some of the same shows you are and have timers set that work fine. Created through experimentation. I never use PASSes and do check them quite often out of habit.
My Daily Show (which was my prime example for the "New" tag errors) timers is:
DVR
Mon-Fri (which since there is no Friday show, skips it) for a specific time.
Early Start: 0
Late End: 5 minutes (since Futurama runs over and you can't start late)
Rachel:
DVR
Mon-Fri for a specific time.
Early Start: 0
Late End: 1 minute
I do have some timers with "new" set and for the most part, lately, they have worked. But I have come up with a lot of conflicts that are not. Some have been hours apart and still conflicted. There is no logic in this software.
You have to resign yourself to the fact that and as much as it p^sses my off when people write that DISH has the best interface, they don't. Otherwise, we wouldn't be here discussing this. It needs a lot of work (in look too, it is so juvenile/primeval). The thing that gets me the most is why is it so hard for them to see, even though I spelled it out for them many times, the logic in how we need things to work. DISH needs to admit that they are lazy and not as "forthright" as the they profess in providing us what they claim they are. AND FIX IT!
Rant done.