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Owner must qualify for relief of debt. The owner must show some financial hardship before the lender will agree to accept less than what is owed. There are plenty of ways to show hardship by including a letter from the owner describing their situation, paystubs, bank statements, overdue bills and so on. By including these types of supporting evidence you can build a great case for why the owner has not been able to keep up with payments and why they will not be able to bring the loan current.
The loan service must be able to participate in a short sale. Most of the times when you talk to a lender or loss mitigation representative, chances are they do not actually own the loan. They may have originated the loan but sold it off to a third party and continue to service it on behalf of that third party. The short sale approval will be accepted or rejected based on that third party.
The property is worth less than what is owed. Lenders will take a hard look at the property value when determining whether they will accept a discount or not. Normally the lender will have a real estate agent drive by and formulate a Brokers Price Opinion (BPO) based on area comps.
The agent will normally do a drive by analysis without seeing the inside of the house. You can normally reduce the perceived value by meeting the agent with your own comps and pointing out all the defects of the house.