I think you’re overthinking it. Bob didn’t know the Simpsons would get TiVo. He just made the ad and broadcast it on the normal airwaves, assuming that (since they spend so much time watching TV) they would see it. He was almost accidentally foiled by their getting TiVo, but then was unfoiled.
Yeah, I didn’t see the fellating either- it was just the basis for some jokes.
I liked the Clippy joke. It wasn’t current, but it was funny.
I work in IT and part of my job is support MS Office, so the Clippy jokes got old and tired years ago. I would expect others not to feel the same on this one.
Jim
I work in IT too, and I thought the Clippy joke was funny BECAUSE it was old.
How could he be sure the Simpsons were the only people to go to the rib joint, then? Or even the first? Even though it was a trap, why wasn’t the parking lot jammed with cars? If the commercial was broadcast, over Channel 6 or whatever, the TiVo was really an unecessary plot device.
Or maybe everybody in Springfield has a TiVo, and the Simpsons were the only family that didn’t skip over the commercial?
A wizard did it. 
I did wonder about this myself, and for the first little bit of the scene, I half expected somebody to come in and ask for a table. (What they did was better.) Maybe Bob had a sign up that said the joint was closed, and removed it when he saw the Simpsons approach. It’d be in character for Homer to see the commercial and leave right away without making sure the place was open.
Does the thing really count as a plot device? The plot works without it, but they put it in as something else to make fun of. They had to start somewhere and they went with “Circuit Circus” the TiVo instead of jumping into Bob’s commercial.
When TiVo first started getting popular, the company gave free units to a bunch of TV writers. Suddenly, as if by magic, the device started showing up in jokes on half the shows on the dial.
Every time I see a TiVO reference on television since then, it reminds me of that and leaves a bad taste in my mouth.