I listed 2 properties for sale from my portfolio.

This will be the largest bond sale in US history coming up which on top of the debt we are also running as well - if we have so much debt to sell I do not see rates going down, I think they may rise (or stay around where they are at). 

They switch banks and ask for an extension and add another $2500 deposit as a show of good faith. 

Still, if you aren't whittling down the number you are analyzing financially to a small subset you see before deciding what to do, you are missing an essential part of getting to the tipping point of expertise in your field.

@Seidy Lasker Wash sale rules apply to stock options if they are deemed "substantially identical" to a security sold at a loss within 30 days, such as options with similar expiration dates or strike prices.

I've talked to two local agents about possible price points to list at, but it almost seems like they are pulling numbers out of a hat.

What about having to break even, or even feed the property every month $200 for those same 36 months, but at sale, could net a $75K-$100K profit?

You will get plenty of that at your office sales meetings, office training, CE training, board and association training.   

As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

You can then measure the cash flow impact versus the potential cash you would obtain upon a sale.