| CPC G06Q 40/06 (2013.01) [G06Q 40/10 (2013.01)] | 19 Claims |

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1. A system comprising:
a server comprising non-transitory memory configured to store program code and at least one processor configured to execute the program code, the server configured to:
receive, from a display device, via a communications interface, an indication of a bond;
determine, according to a predefined tax logic data interpretation process, a tax-neutral fair value of the bond based on a set of bond data and a set of tax data specific to the bond, such that the tax-neutral fair value is reflective of market price data;
determine, using the tax-neutral fair value of the bond and the market price data, according to a recursive valuation path dependent methodology, one or more indicators including at least one of a value of the bond enhanced by a tax option, a value of the tax option and a sell indicator comprising whether to sell the bond and take a loss;
receive and display, via an interactive graphical user interface (GUI) on the display device, the one or more indicators in a results display region of the interactive GUI, the interactive GUI further comprising a user action region associated with the one or more indicators displayed in the results display region;
receive, responsive to the one or more indicators displayed in the results display region, an indication of user input via the user action region of the interactive GUI; and
initiate, at least one transaction responsive to the indication of user input in the user action region.
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