If you are looking to move on to a rental situation and are not concerned about your credit, I would suggest listing the home with a Realtor who is experienced with short sales. It sounds as though the property will be difficult to sell based on its needs, unless the price is right. It will probably require a cash buyer as most lenders will not lend on a property with a roof that is in serious disrepair. All of the costs related to the short sale are customarily taken from the proceeds; so it should not be a situation where you would need to take money from your pocket that you may not have. Assuming you owe more than the property is worth or it will bring in its condition and the current market; your lender will have the final say on the approval of the sale. They may then try to get you to agree to be responsible for the difference or just be willing to forgive the difference. You will never know what they want until you get to that point. You can choose to agree to this or not. If you can't come to terms with the lender and are willing to walk away from the property, it will then be foreclosed on. Good luck to you!