@ Kathy - While you may be one of those "intelligent" negotiators, Banks don't "do short sales without agents all the time". You may work for a local/regional institution that doesn't require it to be listed with an agent but, it sure won't be a Fannie/Freddie property and if you are regulated by NCUA or the FDIC and don't negotiate short sales within acceptable, "Arms Length" parameters, I wouldn't want to be a part of your next compliance exam.
If you take the altruistic motives of the OP you portray out of the situation, he's not "helping him rectify his situation", he's trying to purchase a property that he thinks will be a financial win to him. Nothing wrong with that but let's call a spade a spade and not put some Ghandi'esque spin on it.
And there IS something that makes the homeowner have to list it with an agent. A requirement from the lender and/or Fannie/Freddia also know as the U.S. Treasury Department. They require it be listed under all but the most detailed and exceptional circumstances that are well documented.
Presentation is nice but that's never going to be sufficient all by itself. There are many other required elements to a short sale. Presentation is only one. The best presentation in the world isn't going to make a sure sale go through if it doesn't meet the requirements of the investor/lender/servicer.
"Having the property signatory approval level" is a perfect reason WHY one should list the proeperty with an agent, so the rest of the deal can be reviewed and confirmed to be a proper transaction. All of my negotiators recommend a deal after an exhaustive financial analysis and after verifying that all the requirements of a short sale are met (Like being listed with an agent, executing a 4506T, providing a hardship letter, bank statements, tax returns, Arms Length affidavit, budget, etc..) and then signing off and verifying all of the requirements are met so that when its all done, a subsequent audit from an outside entity or regulatory agent will confirm that it was done properly and NOT just because some talented negotiator thinks it should have been done. Is it the highest and best offer (How woudl you know if it's not listed)? Is it going to close? Did the negotiator run OFAC on ALL parties to the transaction? Is it better than foreclosure? Does it meet minimum net proceeds requirements in the NPV calculations to proceed? Is it arms length? Is anyone getting an inside deal not available to the public at large? Is there PMI? Does the investor need to approve the deal? Does the insurer (If applicable)?. Is it a cash deal or is there financing and if there is financing is the bank (Or whatever financial institution it is) financing their own short sales (That's another can of worms)?
I understand what you are saying and yes, an educated negotiator can make or breaks a deal but that negotiator needs to follow the rules and make sure that everyone else follows the rules and yes, there are rules. If your lending institution gives you delegated authority to approve any deal you feel is a good deal without any oversight whatsoever, I'm not sure that practice would be to the benefit of the institution in the long run.