A data processing system compiles information about account holders, holdings, and other investment-related information. A hypothetical portfolio is generated to provide for a specified payout stream over a defined period of time, statistically evaluated, and compared by means of scaling to determine the best fit scale of the portfolio to the defined criteria. The composition of this scaled portfolio in comparison with the composition of the available assets defines a series of trades. The composition of the level of payout that can be expected to be supported by the new composition of available assets defines a series of insurance trades. Insurance providers can impose limitations and requirements on the assets managed by limiting or stipulating certain settings that a given account can be allowed to have.