In this case even if the project went south and you broke even or even lost money, the equity (debt) you used would still be covered by the income you are earning on the rental property. 

If you don't meet that 12 month seasoning requirement and/or want to hold the property under an LLC, a debt service loan may be a better option.

Combine that with some government austerity and the debt issue improves.

Selling gets a tax free gain and allows you to be more liquid; keeping it allows you to have once in a lifetime cheap debt and have that leverage on an appreciating asset. 

The midwest and specifically Chicago has always been slow and steady - thank you for giving us a shout out @Scott Trench!

That does not require employment or job seasoning instead it uses the rents to qualify and you can take out up to 80% LTV cash.Use the cash to put down on the next 1-2 or more properties as long as the other properties are debt servicing themselves it opens up more opportuities to buy more future assets and increase your passice income.  

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

Well, what would be happening is that your buyer would be buying your house subject to the existing note, since you can't legally sell the property without paying off that note or transferring the debt to the new buyer.

After closing, work on increasing your income, reducing debt, and preparing for a second mortgage.

For now, my immediate goal is to pay off all of my credit card debt (should be accomplished by February 1.), and continue to educate myself on NOI, Cap rate, cash-on -cash return etc.BP community, I am open-minded, willing to take initiative, always willing to be taught something new, but also ready to share any experience or knowledge I have that can help someone else.