I’ve found that if you have a regular 8-5 job, managing a project that may be more than 15-30 min away from where you typically are during the day, is hard to do…unless you’re working with someone (partner or contractor) that you trust and can provide that support for you.

I am on the support team at BiggerPockets.

Support your local bank!

Complication is just complication, it doesn't add any value.The bottom line is the mortgage balance is simply to high for the value of the house, and the rent is to low to support it.

I know you and your partner will benefit greatly from the tools and the knowledge and the support you will find.

It would make sense for them to frame the house, they are already there and they have to support the structure as they bring it down.Maybe they can even consult with the client on what to build, and how to build it cost effectivly and after that they can  facilitate with the permits.

In addition, I'm a student at American University studying entrepreneurship.

The project will not be sold after the build, so that is another issue, after the build, all he will have is 35-40% equity, no stable income to support the loan except for the rent generated from the other doors, I am not sure if the equity will hold some weight when applying for conventional mortgage.

Your moral support fills the little holes in my back from those nasty arrows!

Over Improving would be fixing/renovating a property to a point were you will not recoup that capital investment because the neighborhood comparables will not support a value that high.An extreme example would be installing a $100,000 in ground swimming pool and patio in a home in a neighborhood where the homes typically seller for $85,000.