Quote from @Neal Schadler: I have several properties in Cleveland and the surrounding areas.

Do you have investment properties already or are you just getting started? 

We've been buying properties in the southern US and have had pretty good success.

Are you looking to "house hack", which is living in the property (or 1 of the units) for at least a year and then moving out and renting the unit?

You'd do one schedule E with a business use percentage of 3,300/4,000 or 83% You'd set up depreciation with the full amount of basis, and set business use to 83% The reason two Schedule E may be helpful down the road is if you plan to sell the property. 

I can do the parade of horribles for a personally owned rental property but suffice it to say that it is a long and robust parade and the horribles are horrible.

You must have known the property was in arrears, so it becomes your duty to be in contact with the bank through the process.

TLDR: Quicken (quickbook’s little brother) is super easy, cheap, and still overkill for someone with less than 20 properties.

With the down payment you're putting down (assuming it's at best 25%) with current interest rates, you're maybe going to be scraping a couple of backs cash flow on a Class C+ property. 

He can fight the seller to still buy the property but you are out of the deal and want your money whether he signs cancellation or takes it from his pocket.Key thing is focus on your agreement / contract and your rights.