So many factors are taken into consideration by the short sale negotiator. So before you ask for the moon and the stars, here are things to keep in mind:
1) What is the market value of the property (remember that the negotiator will commission a BPO - broker's price opinion - to determine what the property is worth.
2) What is the balance of the loan - know how much the lender needs to "forgive".
3) How much is your offer compared to market value and loan balance? If you submit a low ball offer, the negotiator will be less inclined to accept the offer and grant credits Are you writing your offer based on fair market value?
4) What other expenses are you asking the seller (in this case, the lender) to pay? Note that most lenders will cover the selling expenses, taxes, insurance, but not necessarily repairs or replacements. In many cases, they won't pay for Homeowner Association fees and fines.
5) Are you writing an offer in a competitive situation where there are surely going to be multiple offers? If so, by asking for closing costs, assuming that your offer price is on par with the others, you may weaken your offer with a request for closing cost credits which result in lower net proceeds for the seller
When you are asked for your best and highest offer, remember that highest offer doesn't always win. Sometimes, terms trump the higher offer. And in many cases, all CASH offer rules!