Hi there,
To answer your questions, in my opinion only....
It sounds like you want to Short Sale your property and take as little loss as possible, which is understandable. Let's look at your options:
If an investor were to make an offer on your property, they are going to obtain as much a discount as possible, because they want to make as much money as possible. I can't see this as a viable option, since you don't want to take more than a 20k hit.
It may be a bit more attractive for an owner occupant to make an offer because the discount they get will be enough to cover estimated repairs (5k), plus obtain a bit of equity (about 15k). This of course is under the assumption that the realtor gave you correct comps and that the prices in your area aren't still falling, in which event may prevent even an owner occupant from bidding. The downside to this is that Short Sale takes several months to complete - at minimum. As well, a Short Sale is never guaranteed to be approved. It may be very hard to find the right buyer who is willing to wait for a *possible* approval. Remember, this is a buyer's market, so they have alot of options right now.
I understand that you need to sell due to medical issues. Is it just not possible to put the money in for repair and list with an agent? Perhaps if you have the cash, but not the time to repair you can offer a credit at closing and just pay out of pocket?
A few brief points...
How much do you trust this realtor? Perhaps get a second opinion. Explain that you need to sell fast and ask what improvements are necessary for that. Also, you may be able to get a contractor to do the work for less than 5k. This is a tough market and *all* professions are hurting.
Not certain how familiar you are with Short Sales, however keep in mind they will impact your credit negatively. Depending on your financial hardship, the fact that you are current on your payments may hurt your chances of successfully completing a Short Sale. This also largely depends on your lender and the negotiator.
Finally, have you considered either straight renting or renting with the option to buy? I know that your property needs work, however there are plenty of credit challenged people with money who want to live in a home. Offer them to complete the work and credit it as a down payment. Just ensure that you request receipts.
This may be the best option to move quick, depending on the rental market in your area and if rent can cover your payments.
No matter what, seek professional advice before you make a decision.
Good luck!
Danielle