I could be wrong... but red flags are popping up.Also you have a house under contract that you signed stating you are a cash buyer and you have no cash and zero intentions of buying.

Green Lights I Used to Ignore the Red Flags:1.

Shawn:If you are renting by the room, lenders will be disposed to see it as a rooming house (whether it is zoned as such or not) - particularly if the appraiser finds distinct evidence (i.e. locks on all bedrooms). 

That being said as well, understanding this is a neighborhood might not pull the best quality tenants (its not a war zone, its more laborers mixed w Sec8), what advice would you give me to fill this w a quality tenant? 

This is outside my comfort zone because it will require me to send stupid low offers every 7 days if I don't have a better one.  

That's a huge red flag.

The land is already zoned for multi fam and the home is already build as a duplex.

@Daniel DeSurra one thing you posted pops up a red flag.

If your profit margin is so slim that ONE MONTH on the market puts you in the red, then you really don’t have any profit margin.  

Doesn't always happen, but it's not a red flag.