I like the idea but most of the servers we manage have out going firewalls to block them from talking to the internet. We produce installed package lists during deployment (as much as possible we run immutable pre-built images and replace the image rather than upgrade in place) which could be sent to a service like this but wouldn't want to start punching holes and adding routes for it. To work as is we'd need to add duplicate canary servers in an isolate environment to talk to the service.