Question: 

Is there any documentation how the software operates from a licensing perspective (centrally controlled, flexLM, etc...). 

Answer:

All of Bentley's newer applications uses our own Subscription Entitlement Service to activate products. CONNECTION Client, a component installed on the client machine, is used to authenticate with us via a login. When an application is opened, it secures a license if permitted by the login. This normally involves communication with our online license server, but offline capabilities exist to either temporarily or permanently use a product apart from an Internet connection.