Abstract: A system is disclosed for identifying potential short sale transactions that can be bundled or combined to produce a beneficial result to the financial institutions involved. Embodiments are directed to the identification of properties matching certain criteria that make them likely candidates for a short sale transaction. Other embodiments disclosed herein assess the value of identified properties and associated mortgages to facilitate short sale transactions, so that mortgage holders can have an accurate assessment of potential losses involved in short sale and foreclosure situations where multiple mortgages are involved. One embodiment provides an assessment of estimated potential losses realized by secondary mortgage holders and/or losses avoided by primary mortgage holders in proposed short sale situations.