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Correct me if I wrong, but doesn't the DVR Priority feature handle this already?
Lets take your example for instance. Let's say I set up the DVR to record new "The Sarah Silverman Program" episodes. You have two other shows that you want to schedule to record at that time as well (we'll just say Show2 and Show3). Since the DVR can only record 2 shows at one time, the DVR has to bump one off. If you set Show2 and Show3 at a higher priority than "TSSP", then it will skip "TSSP" and record Show2 and Show3. The DVR will still record upcoming episodes of "TSSP", so assuming there is a repeat of a new "TSSP" later that night (eg. 3am), the DVR will record it since it isn't already in your list.
I do this all the time with "South Park". I never get to record the newest episode on Wednesday because my wife has other shows she records. Since I set "South Park" at a lower priority on the DVR, it skips it and records a later episode when there are no conflicts with her shows.