A newer house might or might not need less routine maintenance.

I know that for fact (I'm a broker in the state and it's been covered routinely in various classes, etc.).I'll check into local codes to see what they call for.

You could always start with a month-to-month, and if she feels uncomfortable, you don't have to continue down the rental path, but you'll have some great guest quarters and the option for the future to make some extra $ if need be.

At the end, we feel very uncomfortable confronting him about the junk/trash and parking lot issue.

After it is "rent ready" then routine maintenance becomes an expense and is deductible in the year in which you spend the money.

It feels uncomfortable to make offers much lower than the asking price, whether it is real estate or anything else.

He was managing Broker for a mid-sized Property Management and Investor Real Estate Sales company.It seems one of his admin employees owns several investment properties, and in fact the PM company "managed" these, from the standpoint of tenant management and routine service calls.

I routinely browse the crime news on Cleveland.com and this area and this area is relatively quiet.

I'mm not certain about equity to unlock,  and at this point with my DTI as high as it is,  I'd be uncomfortable doing that at this point.  

I'd feel uncomfortable with properties that cash flow negative, but I'm ok with sacrificing some cash on cash return (as long as it's still cash flow positive!)