I make around $110k+ per year, live off around $75K, have a mortgage ($1900/mo for rent, escrow, tax), around $40K in equity, and no other debt. 

The motivation is not necessarily to scale into larger opportunities but rather to achieve better balance and also optimize the performance of the projects and types of projects I currently pursue.I have no shortage of individuals who possess specific skill set who would want exclusive rights to that particular service vertical in return for contributing capital and a partnership interest (construction background and wants to take over all construction duties or someone who is a sales broker and wants to list all of the properties etc.)

There was a trap in roof however I been told by realtor and inspector that it will be replaced and there was no known leaks.

No question is too silly, trust me, I’ve asked them all.

I know a lender that can help with both states that does investment lending for very cheap, it would be worth a connection as you look to build out your team no matter what you decide.

The OP could use it as a template and change it to 30 days and reference the correct county law, or no county at all.

Overpaid slightly, tied up a good bit of capital that no doubt would have been better in the stock market (this past year anyway), and "cashflow" a couple hundred dollars a month.

No landlord is going to want to repaint a rental.

Short answer, yesLong answer, maybe - if the portfolio offsets the negative cashflow and on the portfolio level we meet our positive cashflow metrics then yes otherwise no. 

The stock account is tanking, you see no hope for it to return, and you want to preserve the remainder of the principal;3.