I got my Level One certification in 2000 and paid $18,000 for a Raytheon PalmIR Pro thermal imager that didn't have 1/10 the capability of my new $4,000 FLIR imager.
It is a good tool for selling roofs but I have more fun just piddling with it and discovering new uses. This is my pickup - notice the engine compartment and rear diff are hot. This would be useful to cops trying to find which car in the parking lot just parked there after robbing the bank.

Mike, 13 years ago when I got my first imager, the general public knew a lot less about IR than they know now. Still an uphill climb but at least some mfg are spec'ing IR.
I called my little company Infrared Resolutions, and while I had a blast messing with it, never made a dime on it. I paid $18,000 for my Raytheon PalmIR Pro and gut lucky and sold it for $17,500 to a ship inspector out of Toronto. Never did understand why he was willing to pay that close to the new price.
Still using our old B&W unit, and it's still making us money. You said it very well with the comment about being difficult to monitize such a thing. There's no way we've ever come close to selling that much IR service, but it's paid for itself many times over.
Woody, although I've never tried it, and it would be extremely slow, I guess theoretically you could detect wet insulation with an $80 IR thermometer.
Nick may have already thought of this, but a good angle is to ask architects and and roofing spec writers to write into the spec and the warranty that an infrared roof moisture survey will be conducted 6 months before the roof warranty expires. A lot of times a roof flaw will be letting water into the insulation but it's not showing up as a leak inside.
A couple of months ago, I was in Costco and saw a 2-pack moisture meter and infrared thermometer for about $80. I have used the moisture meter once for work, but haven't had a use for the thermometer other than playing. It doesn't have fancy imaging, but it does give you the temp.
Egg, I was never able to monetize infrared, directly. It is a great tool to use in selling roofs, though. We recently won a Texas county project on foam roofs. Now we all know that foam and infrared aren't usually that useful together but if you're looking for useful clues, they're are to be found.
I was able to differentiate ourselves from the other bidders by showing that the existing foam did not come high enough onto the ductwork and significant energy was being lost in a 10" strip around the tops. The commissioners were intrigued by all the colorful high-tech thermograms.
I won't say which FLIR model I bought because it's top secret and then I'd have to kill everyone who reads this. :-) Suffice that I got a fairly capable imager this time that has wireless, simultaneous digital imaging of the same area you're thermal imaging, etc. A really cool toy. Errr, tool.
Very cool. I'm jealous but there is no way at this stage that I could justify even the $4000 expense for the tool. Magnificent to see though.