But, for instance, someone who has lost their job, probates, someone who has been transferred, needs an immediate sale, it's been a long time on the MLS but hasn't sold, plus properties not up to MLS standards so they won’t list well on the MLS, and other of "life's occurrences" are all reasons some people sell on subject to.

Make sure you check out everything and everyone some of these insurance companies are known to quit paying after a while.

Hey @Henry Lazerow - I would tend to agree that most of the NW side of Chicago 2-4 units don't play out perfectly well for BRRRR deals.I always looked at any potential house hack vs. having to rent - if my overall payments were less than the rent I generally considered that a win.For me...the house hack is just the ticket into the amusement park and then the fun rides come after...getting started can be overwhelming and hard so I can see why people might take a discount.I think one of the keys to strong equity creation is square footage creation which is basically what you outlined with duplexing up or down.

Let me know if you have a good wholesaler as well!

Many of the most successful (read as: founders that are worth well into the 9 figures, have survived multiple market cycles, etc) syndicators I know started by working in real estate for other companies.  

Tenant shall properly use, operate and safeguard Premises, including if applicable, and landscaping, furniture, furnishings and appliances, and all mechanical, electrical, gas and plumbing fixtures, and smoke alarms, and keep them and the Premises clean, sanitary and well ventilated.F.

Well..everyone's story is different.

Look for someone who is an investor as well and can speak to their past transactions with creative financing.

Also, the home appraised for $18K more than the purchase price, so I think that bodes well for the investment.

If the numbers are tight, you will need to short the first as well to get some payment to the second.