No, macOS does not send Apple a hash of your apps each time you
You should be aware that macOS might transmit some opaque
information about the developer certificate of the apps you run.
This information is sent out in clear text on your network.
You shouldn’t probably block
ocsp.apple.com with Little Snitch
or in your hosts file.
Apple should publish information about this system in the excellent — but alas, not comprehensive — Apple Platform Security report, including a clear statement regarding whether they keep logs of these checks. I’m guessing they do not — why would they? — but it would be good to be able to point to a clear statement.