@Chris T. Selling during the slow season is all about price in my opinion; if the house is decent and in a good spot. If it's not in a good location, the price is still the ultimate factor, it'll just need to be lower.
I tell clients when they want to wait until spring to sell they can expect about 5-15% more for their property, but they can also expect to spend that much more on their next property so it's a wash. As an investor, you need to decide if you are willing to price it to sell for this season, or if you're willing to eat the holding costs until the spring and hope you make 10% more on the sale.
You said you've done 3 price drops already since Oct. 6th? That's not good. As a buyer, I'm now wondering why no one else has bought the place and why you have lowered the price 3 times in one month? Your property now has a stigma associated with it due to the price drops. My opinion on price drops is that you have to drop it enough to appeal to a whole separate group of buyers. So if you're priced at $250k, a drop to $245k isn't going to attract very many new eyes.
I'm not sure what your market is like, but if it were my property here I'd unlist it, maybe try to get a 6-month tenant in there, and then re-list.