If I need to advertise and find a tenant externally I feel like I am capable of doing that too. 

Now that you’ve defined the nightmare, what are the more probable or definite positive outcomes, whether internal (confidence, self-esteem, etc.) or external?

. $7,000,-Phase 2: Roofing/Exterior Windows and doors. [5 days] Close up external side door between living room and kitchen, patch siding, patch wallReplace windows, replace front entry door, power wash house/deckRestoration of vinyl siding which includes power washing and replace any missing pieces of siding.

He is the only share holder and there will never be any external partners.

To separate them you will need to go through a subdivision.It’s not a full condo conversion if you are only separating the buildings and not each unit.You will need to talk to land sourveyor and estimate the cost.It is likely that you will need to upgrade the services and some utilities, also you may need to fire rate the external walls of each building.

Your exit will be to another investor and that sentiment can change depending on external factors like interest rates, risk free return rates etc.

I may selectively cold call after 'driving for dollars' or kind of hand picking properties that may work well. 

I scan everything to an external.  

I had to rip out all the trim and even the doors (internal and external !

We did do our due diligent in marketing the property through our external websites and other sites such as craigslist.