Making the wrong hire, overlooking the risks, taking on too much debt.

Analyze properties by looking at gross rental income, operating expenses, and the debt service coverage ratio (DSCR above 1.25 for rentals).

If you are trying to raise a few hundred thousand to buy another 4-6 unit property, while I would not invest in someone with less than a year experience, I am guessing some of your pilot friends, other friends, or family members may be willing to chip in.Now, if you want to jump from a triplex to 80 units, raising 4-5mm of equity and another 4-5mm in debt, than I would just manage your expectations. 

The number of DSCR (Debt Service Coverage Ratio) loans a lender will offer can vary depending on the lender, your financial situation, and the property cash flow.

I was able to eliminate that expense just by switching to baselane because I can do it myself now.

If you just borrow more money, you are getting deeper in debt. 

Taxes : Taxes have been a brewing crisis nationwide for sometime, Chicago is another prime example of a major municipality struggling under high debt load.

If there is no debt service probably 30% is still going of the rent is still going to operating expenses which means that you only made about 480k or so. 480k rents + 800k property is the same 1.3million roughly.

Even if a title company were to manage the setup making sure all parties are paid, the cheap debt and cash flow would not be enough to be enticing to any investor even if midterm rental could yield a healthy return. 

Eliminate debt, establish a budget, and save.