Good luck recognizing that level of detail! This isn't that type of imagery. You can tell just barely tell a truck from a car and can definitely tell the color of the vehicle, but that's about it. You're describing 1cm imagery from drones, not satellite imagery.

Regardless, insurance companies are big customers for similar reasons. Recognizing swimming pools in imagery is tougher than you'd think, but a classic thing (and real) that gets brought up is your insurance company raising your rates because you put in a pool and didn't tell them. Insurance companies would love to (and sometimes do) detect that from satellite imagery instead of boots on the ground.

Either way, those are big companies / big contracts, rather than individuals buying imagery directly.

In Puerto Rico, roofs are flat and get dirty within a few months. You absolutely can easily determine when it was last powerwashed as well as when it was last sealed.

Sealing will leave you with a pure white roof for about a month or two. Powerwashing will leave you will light to medium gray. They'll turn dark gray to black within a few months in the parts where the water pools.

It's different for dyed sealant, but there is a time while the work is being done where old sections are stripped back and the new material is drying. Lots of false positives from HVAC work etc. though.

If this is such an issue, why not have sloped roofs? (Just curious)

Actually the roof example can be done at scale cheap enough for a local contractor to market. I'd use hyperspectral but 30 cm optical might work in sure 10cm would. Thanks for the suggestion!

One might not need that level of detail to put together that message. If you already have a database of car ownership by address, figuring out which vehicle-like blob is parked in the driveway is not a hard problem. Worst case you accidentally send an advertisement to somebody that's not as personalized as you were hoping.

I think I'm going to vomit :(

Don’t do that outside though! You’ll get ads for gastrointestinal medication.

Local contractors driving by your home can do the same thing.