Roomba walks back plan to sell maps of your house to Amazon and Google

Ours would. Well, mostly.
1950ies housing might be a bit sketchy.
The state building codes in their current form, which also include regulations on documentation and archives, were introduced in 1962. Regulations before that go back to the early 19th century, but are an odd mixture of state and local regulations that would sometimes be incoherent or even contradicting in some points. So everything built after 1962 would have some sort of paper trail, and that includes modifications1) on buildings that already existed in 1962.

1) Modifications that require approval by the planning department. Which includes anything that touches the structural design or fire safety. The rest varies somewhat. If it’s a building listed for preservation, practically everything needs approval. Unlisted buildings: any significant changes. Changes both regarding the building itself and what it is used for require permission. For instance, changing an office into a flat or vice versa, or changing a retail store into a restaurant, requires approval. If you do not use a building in the way it was approved, you’d not only be in trouble with the planning department, but also your insurance company. There are usually clauses in the contracts that make any non-approved usage a breach of contract and trigger the “no soup for you” clauses.

But commercial plaza, definitely. Buildings like that are checked every five years by the local planning department and the fire department; the focus being changes done without planning approval and anything related to safety in general and fire safety in detail. They are also checked for any deviations in the as-built from the as-approved before they open for the first time, of course.

Condos and such, that would depend somewhat on the age and size, as the building codes for larger structures (with a larger number of people inside) are stricter, and that means a larger and more detailed set of documents that has to be forwarded to the planning department for approval.

The planning department keeps a file on every building for as long as it exists, from the building permit to the approval of its demolition. What the file contains in any given case depends somewhat on the age of the building, see above. In general, its everything ever submitted to the planning department as required by state building code, plus everything else they managed to lay hands on.
When a building is demolished, the planning department closes their file on it - and forward it to the city archives.

So, unless it’s a building that has somehow managed for decades to fly completely under the planning department’s radar, so to speak, you’d find something in the files that is at least a close approximation to the existing condition.