I can run and model numbers and am a CPA so comfortable with the finance side of things.

There is no such absolute rule or mandate for REI - it is up to you on your comfort level with your cash flow versus total investment versus appreciation potential.If I followed that rule, I would have missed out on a LOT of great opportunities over the years.We bought a house in Jones Valley in 2017 with negative cash flow - why? 

My ultimate goal is to acquire enough real estate to achieve financial freedom, allowing me to travel, provide a comfortable life for my family, and teach my children about discipline, financial literacy, and the wealth-building potential of real estate.I’m here to learn, share, and connect with others who share this passion.

I think the before vs after pictures really speak primarily to your experience and ability to execute a project so it can help lenders gain comfort with future projects and allow you demonstrate what level of detail you except out of your contractors.

If it is in a C/D area I would not be comfortable with breaking even.It looks to be between Blue Hills and the research hospital.

Deviations from the Private Letter Rulings will significantly increase your risk of structuring this type of advanced 1031 exchange.You should discuss this more advanced 1031 Exchange structure in greater detail with your legal, tax and financial advisors to determine your comfort level with this complicated 1031 Exchange structure and the inherent risks involved.

If you and your wife are on the same page, I say absolutely go for it.Don't worry about the naysayers telling you to invest out of state if that's not something you're comfortable with right now.

If he doesn't need the cash now, you could also negotiate a split you're comfortable with to get him the return you and he feel he should have at the point you refi when the balloon payment comes due. 

Company is called Comfort Capital.

In this option your agent would either get paid from you directly in your closing costs OR from the seller via seller concessions.like Russell said, if you are comfortable with the transaction and understand what you are signing and you don't need things explained and you have connections with inspections and title companies then go for it.