@Jesse T. - Is the question that you are trying to answer "Do more expensive homes take longer to sell?" or "Do homes priced correctly sell faster than homes that are overpriced?". Either way, I think that this will be hard to answer. I would assume, on average, that more expensive homes take longer to sell, as the buyer pool is much smaller than your median priced homes. This can be proven by looking at the distribution of homes sold in different price buckets. However, with that being said, a luxury home that is competitively priced has the potential to sell faster than an average home that is over-priced. Other qualitative factors come into play as well, like desirability of the neighborhood, condition of the property, etc. The problem with analyzing large data sets is that it is difficult to account for these different variables.
I think your question is "Will the cost savings in terms of holding costs outweigh the price reduction on the house I am selling, assuming this will allow me to sell faster". I don't think this is necessarily a statistical problem, rather (like most real estate problems) a situational analysis. There are a few pieces of information you are going to want to know in order to perform the analysis. First, you are going to want to know the trigger price of your home is, aka at what price point will my home be considered FMV and what is the average DOM for homes that are considered FMV. Next, you will need to look at recent sales that, in your opinion, were priced below FMV and determine if these houses sold in fewer days than the average. Pay special attention to price changes and list price vs. selling price, as this could seriously skew the data. You may be able to determine if there is an inverse correlation here that exists between selling price and DOM. With enough data, you could even quantify "a price reduction of X translates into a reduction in DOM of Y". Then, you can determine if the cost savings outweigh the loss of revenue. Without looking at any data, I would assume that the amount you will have to drop your price by will not be recouped cost savings. However, there are many things that could change this.
