I manage properties remotely and can handle all the leasing/management pretty easily with my team.

Is this a 2 bedroom apartment that is currently being leased (in the eyes of the CHA) as a 1 bedroom apartment?

I am new to the game with 1 property leased to section 8 under my belt and was about to buy another.

Here's a little background on Tenant situation...has 2 or 3 young kids, an adult sister, an aunt with her male friend and the lessee has a male friend, that all appears to live in the apartment but aren't on the lease.

With the tech I am using (a lesser known PMS) I am able to automatically screen guests, get their selfies, write leases, and collect deposits in my work flow even for Airbnb guests.

There would be rent of $ 8 K a month on a triple net lease.

In general, DSCR loans will require the property to be either leased or at least "Rent Ready". 

The newest outdoor is still advertising 1st month free as they haven't filled up, and I spoke with the climate controlled owner/builder yesterday (he's a pretty big REI in the area), and he made it sound like he hadn't leased a single climate controlled unit since they opened a few weeks ago.I recently purchased a 140x45 warehouse with low ceilings and had debated doing self storage, but my market seems very saturated.

Whether you’re dealing with non-payment of rent or other lease violations, this resource explains what landlords need to know to remain compliant and protect their investment. 

Haggle with them to a maximum 60 day timeline) as you need time to renovate and get it ready for spring/summer market when most peoples leases are up.