My realtor calculated he would also need to drop the sales price by $40k to break even with the previous deal, which I highly doubt he would entertain.

There maybe an investor in your area who would be entertained if the deal has enough meat on the bone to JV with someone that can bring the balance sheet to the table.

Alas, I don’t feel like I have a lot to bring to the table so to speak so not sure that idea could even be entertained.  

Disclaimer: This post is for entertainment and is not to be construed as legal advice.

@Luis Ramirez First thing I'll say is that the TV shows about house flipping are good for entertainment, but nothing beyond that! 

But if you're having trouble building up your confidence it's best to avoid them for now and surround yourself with Big thinkers.I remember that quote in the 80's on that video show on BET (before it became Baffoon Entertainment Television):Small mind talk about people.Average minds talk about Events.Big minds talk about Ideas.Notice how everyone you know who is successful don't waste their time talking about he said/she said ........or who fought who.

We have also entertained the idea of purchasing a out of state property and paying for a PM but from what I've read, the income is only about $200 month average?

Not a great place to be coming from, assuming people posting on this site are lying or have no idea what's going on.Sorry but I’ve seen enough people that equate cash to mean “money laundering drug dealer” to at least entertain the thought that the guy wanted cash, and the rest was an assumption by OP. 

Banks/Lenders are entertaining short sales all day long in lite of the current market conditions.

I'm late coming to this thread and do not know the floor plan of your duplex, but have you entertained using a ductless split heat pump - one per unit, perhaps with two heads each if warranted by the size and layout.