An improved and automated ASP-delivered loan workout system, inclusive of communication architecture and software method that assists a user in improving the dialogue and counseling sessions between user, borrower, and other involved parties, and which increases loan servicer efficiency while decreasing the time and expense necessary to process loss mitigation cases-including identification of an appropriate financial workout solution, via the use of logical decision tree-based interviews-increases the rate of identification of viable loss mitigation options, and selects and manages the best loss mitigation solution, all in real-time, and within investor and lender requirements, within loan guarantor and insurer conditions, and in compliance with rapidly changing industry standards and government rules.