.... I almost wonder if there is a massive radio frequency near theirs at that location, and thus each time you drive by, it screws them up on que?
Funny, but I was thinking along the same lines. While it's a great idea and a real lifesaver, the current TPMS systems are really first generation and less than perfect. To really appreciate the magic of RF transmission systems, you have to realize how innovative yet fragile they are.
4 coin-cell powered 315mhz transmitters sealed in a permanently damp environment are expected to last for 7-8 years minimum. They put out a little peep of data (nanowatts?) that must be logged by the receiver. There is all sorts of leeway and allowance for missing or corrupted data for an extended period of time programmed in, otherwise you would be constantly annoyed by false warnings. There are many things that can interfere with good TX/RX - both externally to the van, or because one or more of your sensors has a problem. My Sienna has had two sensors replaced as defective.
What they do respond to very quickly is a strong signal showing pressure loss at speed. My wife experienced that on the highway after hitting a road hazard.