I work for an insurance company. The company currently pays for lo-jacks for high-end cars, and has often studied the cost of installing some variant of it for the entire fleet.
A GPS car tracker costs a lot less than what you're quoting, when purchased in bulk from China (I don't know about reliability figures though :) ). I think it was in the U$ 15 range for the entire thing. Certainly not the armored thing you're describing, which sounds pretty expensive.
And the cell phone data plan could be negotiated way down (I think your estimate is correct, about U$ 1 or 2 per month). What I pay here as a consumer in Uruguay is less than U$ 5/month for 384 megabytes. Getting a fix is definitely a problem, but you can track it until it gets inside wherever it lost the signal (hopefully it's a warehouse).
That said, there's a lot of low-hanging fruit to start putting GPS trackers on pallets :) (I still don't see them being ubiquitous with pets and other higher-value items to track).
If it wasn't feasible for cars (MUCH more expensive than pallets), then I agree with your estimate that it won't happen soon, but it's going to be possible sometime in the near future (and somebody is going to be ready for that, and make a killing).