I suspect my pro forma would show this as negative cash flow. 

While you wait for everyone to answer you, I suspect you'll get quicker information by doing some searches here on BP, for terms like rehab funding, funding for flips, hard money, private money, construction loans, rehab loans, etc.The topic has been discussed exhaustively here, and continues to be discussed almost daily.

I’ve been suspecting that with contractors as I’ve been getting work done to fix this place up, but I’ve been lucky so far.

Based on investor calculations (2 percent rule, double rent rule, and others I've read about), I suspect that a person looking to buy the home to live in will always be willing to pay more than an investor.

I suspect the answer is no to both questions.

Additionally, submetering is permitted under Ohio law so long as the landlord does not fail the Shroyer test thereby running afoul of PUCO rules. https://www.puco.ohio.gov/be-informed/consumer-top...We've never had to evict a tenant who was paying rent but refusing to pay utilities in our county but I suspect that our county would allow it provided that the lease clearly specified the responsibility for the water bill.

We suspect the units he still owns in the building he isn't paying full HOAs dues on because there are discrepancies in the amount collected each year in the building compared to what it appears should be getting collected...although don't and can't get proof because his family member does the books. 

This gives you a reminder to inspect and raise the rent, which I suspect you have not been doing.

I never would have suspected so many involved in all of this.

Rehabs are pricy here and workers are in short supply, like everywhere I suspect. 5.