System(s) and method(s) to incentivize adoption of time-dependent customized insurance benefit(s) are provided. A provider of insurance benefit(s) incentivizes adoption of the insurance benefit(s) in exchange for knowledge of operation characteristics of an insured entity. Knowledge is cumulative and collected from the insured entity and environment in which the entity operates. Incentivation is accomplished at least in part through generation of incentive offer(s) based on available knowledge, which is associated with an operator of the insured entity rather than with the entity itself. The operator can regulate the scope of exchanged knowledge, and received incentive offer(s) and related content. Incentive offer(s) can be directed to provision of insurance benefit coverage that is adequate to current or nearly current operation condition(s); discounted real-time or nearly real-time insurance benefits; or subsidized service(s). Offered incentives can be afforded at least in part through monetization of available knowledge via commercialization thereof or targeted advertisement.