It's very common to have a squeeky clean woman dating a "bad boy" with terrible credit and criminal history.

Do you utilize your CPA all year round or just during tax time? 

You will lose more when it's vacant and you have to cover utilities, particularly in a colder climate.

The common phrase I've heard over the years is the best time to buy real estate "was 10 years ago".If you buy with cash flow and have financing that doesn't have a short-term balloon, you should be able to ride out any storm and be positive on the other side.

The most common issue I see is an investor, many out of state, buying properties in rougher neighborhoods because it's cheap, not realizing that it's active income and much more difficult to rent out and keep good tenants but there's also an issue finding legit contractors to work in those areas and they often will charge higher for the risk. 

Is that space better utilized as something else for the small ROI.

I don't know how to go about changing to 3 addresses, how to address utilities, heating and any other requirements (e.g. 2 doors per dwelling or 1?). 

@Nik Moushon The template is a great tool we utilize throughout the process. 

Insurance and utilities. 

When I sent the approval letter with details about utilities, move in date, and the requirement of renter's insurance, he outright refused to purchase renter's insurance.