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"The second was the amount of private information that could be gleaned from the process alone. X-rays, infrared scans, phone taps, etc, would all allow officers to learn more than whether or not someone has done something illegal."

Not if it's all run through a computer sitting in the police cruiser which then only tells the police if it finds something positively identified as something illegal. The dog can smell the air freshner, any food in the car, rust, or any number of other perfectly legal things. The value in a drug sniffing dog is its signalling when it smells drugs. It's not supposed to alert officers if it smells a ham sandwich, much like the computer in the cruiser shouldn't alert the police to the vehicle's occupants' skeletal structures. From what's said here, software that simply gives a warning if it detects something naughty in the car would be perfectly alright.

"No proper reading of this ruling would allow the use of any of the other methods you listed without a warrant."

I'm not saying it allows everything all at once, but it's definitely a move away from 'plain view', which was to protect the lives of officers. Now we're dropping into extra-human-sensory perception. We could fire gamma rays through the car and map the molecular structure of everything inside the car. Then our handy dandy computer can pop us out a warning if there's anything in there it doesn't like. We're still within this ruling. It'd probably take another few rulings, but it's this precedent that has me worried.

"You can't search everything."

Given the proper equipment and a few advancements in technology? Sure you could.

"If the dog sniff could let the officer know the guy's shopping list in addition to the location of the large stash of illegal contraband this guy was carrying, then the search, like the thermal imaging scans in Kyllo, would have been unconstitutional."

So again, we adjust our software to automatically disregard anything that's not illegal. Now your officers have no way of gaining information about legal things happening or present within the vehicle.

"Caballes acted nervous, his car smelled of air freshener, and he said he was moving but only seemed to have a couple sports jackets in the car. Now... that wasn't probable cause. Nobody claims that was probable cause. If the officers thought those actions gave them probable cause they would have opened the trunk without first bringing out the drug dog."

Agreed.

"the police were justified because the dog sniff did not invade Caballes' privacy."

Neither, technically, would using a mind-reading machine so long as it works from a distance (oh boy that's going to be a fun bridge to cross). My point is that the distance from the vehicle or its contents and the manner of extra-human sensory data collection and analysis used is irrelevant because the search itself resides outside the scope of 'plain view'. It's really no different than using a machine. A dog is a machine - a biological machine. Its use here is to bypass the restrictions on what an officer can and cannot search. The cops couldn't open the trunk to search it legally so they found a way to conduct their search without opening the trunk. The fact remains that a search was still conducted. Any which way you slice it, if a human can't walk up to the car and see/taste/smell/feel/hear something, then any attempt to locate it constitutes a search. Whether that attempt is made by a dog with a hypersensitive sense of smell or by a sophisticated scanning device that uses physics and software analysis is irrelevant. The attempt itself is the search, and that search itself is the problem. In my opinion, under the 'plain view' doctrine, in order to gain knowledge beyond that which can be perceived by a human police officer, probable cause is required. While the SCOTUS babbles on about semantics, where the air is, whose air it is, etc, they're completely forgetting the fact that there's a reason those cops can't pop open the trunk and search it. It's not because they'll untidy his vehicle by doing so - it's because the search itself is intrinsically contrary to the protections provided by the Constitution to the people of this country.

"Now, if you actually knew of scientific evidence that the drug dogs will react to Puperoni treats in addition to illegal substances, you might have a privacy case."

There are two angles here. One is whether any police drug-sniffing dog in use can be made to react to something other than the drugs. If it happens once, you're right back into the realm of potentially giving information to officers about completely legal items contained within the vehicle. The second angle is whether the dog can be fooled or encouraged into giving a false positive by its handler. If a certain tug on the leash or a swift kick in the rear can made the dog give a false positive, then you're right back where you were. My object, however, continues to live way back at the start of the actual search, which began when officers attempted to gain information about the contents of the vehicle above and beyond that which they could normally perceive without even having probable cause.

From what's said here, software that simply gives a warning if it detects something naughty in the car would be perfectly alright.

You're right... it would. And I wouldn't have a problem with such equipment being used. Why do you?

it's because the search itself is intrinsically contrary to the protections provided by the Constitution to the people of this country.

I think it all goes back to what you think the purpose of the fourth amendment was. Was it to keep big brother from catching the bad guys? Or was it to protect us from big brother's harassment?

As long as this X-ray + software package isn't used to harass people (i.e. the inconvenience is kept to nill [that includes the provision that cops can't stop people just to run this scan]) and as long as it doesn't alert the officers about my ham sandwich it doesn't violate the framers' intent.

One is whether any police drug-sniffing dog in use can be made to react to something other than the drugs. The second angle is whether the dog can be fooled or encouraged into giving a false positive by its handler.

Both of those concerns speak to whether the dog sniff gave the cops probable cause to open the trunk... not whether they needed probable cause before letting the dog sniff the trunk. The court addressed the second issue but not the first... (though they noted that there's no evidence that false positives are a problem).