Let’s say you have to drop it down to $250K to sell it. Using a very conservative rate, you could likely earn 4% risk-free on that money. That nets you $10,000 per year, or $833 per month. If you were able to get 5% long-term, that would put you at around $1000 per month in interest.
So, depending on the actual net you get out of the sale, you will be able to do almost as well return-wise as you could in something that is entirely risk-free (3 CDs with each < $100K) and requires no effort on your part as you would be able to do by renting out the house. Factor in the property taxes each year, the capital loss deduction you will be able to take into perpuity, having to deal with tenants, money to fix it up, and all the other crap (potential liability) that comes with owning a rental, and I can't see a whole lot of reason for not trying to sell the house and then just putting that money into a CD or Treasury bill or something.
Basically, you need to figure out how much per year in risk-free interest it would take to equal the net rental income you could get, and then figure out what you would need to net out of the sale to get there. You may find that you can drop the price quite a bit more because risk-free, no-hassle interest just has so many advantages over trying to make money off a rental house.
