I would ultimately want to add one investment property building per year, and specialize in 3 to 6 unit products to build a large portfolio of those products in the local Chicago market around Midway airport and the city itself. 

This trip has been very productive because for being here only a few days, I was able to see which part of town to possibly invest in and to stay away from.I was hoping to meet and personally shake hands with James Wise and Tom Ott, since I follow them on social media like YouTube, but I think these guys are busy--which is a good thing for their business.

To get to this level, you could either pay down the loan through payments or make some improvements to the property that raise the value or wait for the market to appreciate on it's own. 

You get the discount up front but may also get to raise rents sooner if they find a new place in 6 months.

An air bnb with less than 7 days raises to section 162 definition of a trade or business all day long though. 

Ive used Watson PM (Good service, not very aggressive with raising rents), RealSource (Good with raising rents) and Real PM & Realty (Average service)  What is the issue with the 3 previous? 

One consideration could be refinancing the current loan back to a 30-year, though looking at what you state as your current loan and compared to today's rates, I think it would actually raise your P&I.So, based on what you've described, it seems like renting it probably isn't the best approach here.Also, on selling it, you may be a bit high with an expectation of $50,000 net.

Utilities are in, phase one of the roads, curbs, gutters and water retention has been completed as well.I have received approval from the municipality to build the project as duplexes that will optimize cash flow and raise the number of finished units to approximately 300.I owe 1.25M and need 1.05M to finish the roads, curbs, gutters, and water retention.The first lien(1.25M) is overdue and was intended only as a bridge.The finished value of the subdivision would be 3.4M -4.5M as finished lots, depending on the comparables the appraiser uses.I have also found a lender that will lend to take the first out, but his points are high, it's not hard to get very expensive in points on a loan size like this.I am outside the Phoenix and Tucson markets in a smaller but rapidly growing area.

I will raise the money.

Hey MattI’m one of those guys that had hangups when someone mentioned vinyl flooring because it raised images of that cheap, peeling laminate that was easily cut and invariably began pulling up, flaking and cracking.