Ultimately, you still want to be confident that she will be able to pay the rent and the more you allow your requirements to slip, the more likely your tenants will be giving you headaches in the future. 

to follow up on Pratiks thought.. just send a courier in with your offer in writing and keep it arms length.. the courier can just say man I am here to walk you through these papers and sell the house.. if he balks he balks.. but your not putting your self in the middle have the buyer be an LLC etc.

With 199A (assuming I am confident I can qualify), that might even drop a bit more. 

I would also like to own a billboard property and was wondering how to go about that it would I just buy land and look for bilboreda to put up my self?

I need help converting my commercial warehouse into climate control self storage. 

Also, especially with any friends / family borrowing, making good on the original agreement builds trust / confidence / reputation / etc.

and feel confident enough to start wholesaling.

While you did not mention how many bedrooms or baths each unit is, so I cannot properly speak to the approximate rent, I am confident that it would not be near as high as 3500 a month.

It is hard to judge how properties did in the last downturn because of too many variables to include owners living pay check to pay check with no reserves, paying 40% commissions vs self managing, location, quality, etc...

Listed today for $2000 and I'm getting lots of interest and I'm very confident it will rent fast.