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First, are the two remotes for each of the trucks the same? Different GM models sometimes use different transmitters. To determine if they're the same transmitter look on the back of your Tahoe remote and Silverado remote at the part number (something along the lines of "GM: 15186200"). I believe the part numbers will have to be the same for this to work. If they aren't the same you can check to see if they're interchangeable by trying to program the Tahoe remote for the Silverado and the Silverado remote for the Tahoe.
Assuming the part numbers do match (or the remotes are interchangeable), I'd have someone work with you and go through the programming sequence with both vehicles at the exact same time. This is just a guess, but I'd bet it'd work. If it doesn't work don't give up, there should be some way of doing it because at my work we've got a fleet of '03 Tahoes and one keyless entry transmitter works on several of them (that's the way they came from the dealer).
If you do get it to work let us know.
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